Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2020; 31(20): 1976-2012
DOI: 10.1055/a-1288-8240
DOI: 10.1055/a-1288-8240
account
Modular Approaches to Cyclopentanoids and their Heteroanalogs
S.K. thanks the Department of Science and Technology, Ministry of Science and Technology, India (DST) for the award of a J. C. Bose fellowship (SR/S2/JCB-33/2010) and CSIR for financial support. Y.T. thanks IITB for the award of an IPDF position. Praj industries are gratefully acknowledged for the Pramod Chaudhary Chair Professorship (Green Chemistry).
Abstract
Cyclopentanoids and their derivatives are interesting targets in synthetic organic chemistry due to their extensive applications in various branches of chemical sciences like pharmaceuticals, natural and non-natural products. In view of these applications, several synthetic strategies have been developed in the past three to four decades. In this article, we describe our work towards the synthesis of cyclopentanoids and their heteroanalogs involving diverse synthetic strategies during the past two decades. Among these, photo-thermal olefin metathesis, ring-closing metathesis, ring-rearrangement metathesis, cyclopentane annulation, [2+2+2] cycloaddition and Diels–Alder reactions have been used to assemble cyclopentane rings of diverse architecture.
1 Introduction
2 Synthesis of Spiro[4.4]nonane (A1) Derivatives
3 Synthesis of Octahydropentalene (A2) Derivatives
4 Synthesis of Linear Triquinanes (A3)
5 Synthesis Spiro Triquinanes (A4)
6 Synthesis of Angular Triquinane (A5) Systems
7 Synthesis of Hexahydro-2′H-spiro[cyclopentane-1,1′-pentalene] (A6) Ring System
8 Synthesis of Dispiro[4.1.47.25]tridecane (A7) Ring System
9 Synthesis of Hexahydro-1H-3a,7a-propanoindene Ring System
10 Synthesis of Linear Tetraquinanes (A11 and A12)
11 Synthesis of Tetrahydro-1′H,3′H-dispiro[cyclopentane-1,2′-pentalene-5′,1′′-cyclopentane] (A13) Ring System
12 Synthesis of Decahydro-1H,8H-dicyclopenta[a,h]pentalene (A14) Ring System
13 Synthesis of Dodecahydro-1H-dicyclopenta[a,d]pentalene (A15) Ring System
14 Synthesis of Octahydro-1′H-spiro[cyclopentane-1,2′-cyclopenta[c]pentalene] (A16) Ring System
15 Synthesis of Decahydrospiro[cyclopentane-1,7′-cyclopenta-[a]pentalene] (A17) Ring System
16 Synthesis of Compact Tetraquinane (A18)
17 Synthesis of Higher Polyquinanes
18 Conclusions
19 Acronyms
Key words
cyclopentanoids - metathesis - cycloaddition - allylation - Grignard reaction - Fischer indolization - Claisen rearrangementPublication History
Received: 31 August 2020
Accepted after revision: 12 October 2020
Accepted Manuscript online:
12 October 2020
Article published online:
18 November 2020
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Heatley NG, Jennings MA, Florey HW. Br. J. Exp. Pathol. 1947; 28: 35
- 1b Comer FW, Trotter J. J. Chem. Soc. B 1966; 11
- 2a Umezawa H. Heterocycles 1979; 13: 23
- 2b Nishimura Y, Koyama Y, Umezawa S, Takeuchi T, Ishizuka M, Umezawa H. J. Antibiot. 1980; 33: 404
- 2c Takeuchi T, Iinuma H, Iwanaga J, Takahashi S, Takita T, Umezawa H. J. Antibiot. 1969; 22: 215
- 3 Nozoe S, Furukawa J, Sankawa U, Shibata S. Tetrahedron Lett. 1976; 195
- 4 Srikrishna A, Dethe DH. Org. Lett. 2003; 5: 2295
- 5 Groweiss A, Fenical W, Cun-heng H, Clardy J, Zhongde W, Zhongnian Y, Kanghou L. Tetrahedron Lett. 1985; 26: 2379
- 6 Zhang J, Ling W, Yang Z, Liang Y, Zhang L, Guo C, Wang K, Zhong B, Xu S, Xu Y. Mar. Drugs 2019; 17: 101
- 7a Kaneda M, Takahashi R, Iitaka Y, Shibata S. Tetrahedron Lett. 1972; 4609
- 7b Hog DT, Mayer P, Trauner D. J. Org. Chem. 2012; 77: 5838
- 7c Qiu Y, Lan W.-J, Li H.-J, Chen L.-P. Molecules 2018; 23: 2095 ; and references cited therein.
- 8a Bohlmann F, Zdero C, Jakupovic J, Robinson H, King RM. Phytochemistry 1981; 20: 2239
- 8b Coates RM, Ho Z, Klobus M, Wilson SR. J. Am. Chem. Soc. 1996; 118: 9249
- 8c Weyerstahl P, Marschall H, Seelmann I, Jakupovic J. Eur. J. Org. Chem. 1998; 1205
- 9a Marco JA, Sanz-Cervera JF, Morante MD, García-Lliso V, Vallès-Xirau J, Jakupovic J. Phytochemistry 1996; 41: 837
- 9b Weyerstahl P, Marschall H, Schulze M, Schwope I. Liebigs Ann. 1996; 799
- 9c Wang CM, Hopson R, Lin X, Cane DE. J. Am. Chem. Soc. 2009; 131: 8360
- 10a Pinto SC, Leitão GG, Bizzo HR, Martinez N, Dellacassa E, dos Santos FM. Jr, Costa FL. P, de Amorim MB, Leitão SG. Tetrahedron Lett. 2009; 50: 4785
- 10b Joseph-Nathan P, Leitão SG, Pinto SC, Leitão GG, Bizzo HR, Costa FL. P, de Amorim MB, Martinez N, Dellacassa E, Hernández-Barragán A, Pérez-Hernández N. Tetrahedron Lett. 2010; 51: 1963
- 10c Melching S, König WA. Phytochemistry 1999; 51: 517
- 10d Pinto SC, Leitão GG, de Oliveira DR, Bizzo HR, Ramos DF, Coelho TS, Silva PE. A, Lourenco MC. S, Leitão SG. Nat. Prod. Commun. 2009; 4: 1675
- 10e Hong AY, Stoltz BM. Angew. Chem. Int. Ed. 2012; 51: 9674
- 11a Anke T, Heim J, Knoch F, Mocek U, Stefian B, Steglich W. Angew. Chem., Int. Ed. Engl. 1986; 24: 709
- 11b Han JW, Oh M, Lee YJ, Choi J, Choi GJ, Kim H. Molecules 2018; 23: 2377
- 11c Huang Z, Huang J, Qu Y, Zhang W, Gong J, Yang Z. Angew. Chem. Int. Ed. 2018; 57: 8744
- 11d Anke T, Heim J, Knoch F, Mocek U, Stefian B, Steglich W. Angew. Chem., Int. Ed. Engl. 1985; 24: 709
- 11e Shinohara C, Chikanishi T, Nakashima S, Hashimoto A, Hamanaka A, Endo A, Hasumi K. J. Antibiot. 2000; 53: 262
- 12a Marson CM. Chem. Soc. Rev. 2011; 40: 5514
- 12b Kotha S, Deb AC, Lahiri K, Manivannan E. Synthesis 2009; 165
- 12c Franz AK, Hanhan NV, Ball-Jones NR. ACS Catal. 2013; 3: 540
- 12d Bartoli A, Rodier F, Commeiras L, Parrain J.-L, Chouraqui G. Nat. Prod. Rep. 2011; 28: 763
- 12e Saragi TP, Spehr T, Siebert A, Fuhrmann-Lieker T, Salbeck J. Chem. Rev. 2007; 107: 1011
- 12f Dürr H, Gleiter R. Angew. Chem., Int. Ed. Engl. 1978; 17: 559
- 12g Quintavalla A. Curr. Med. Chem. 2018; 25: 917
- 13a Majetich G, Shimkus JM. J. Nat. Prod. 2010; 73: 284
- 13b Gabriele B, Mancuso R, Veltri L. Chem. Eur. J. 2016; 22: 5056
- 13c Chanda T, Singh MS. Org. Biomol. Chem. 2016; 14: 8895
- 14a Khan MA, Nabi SG, Prakash S, Zaman A. Phytochemistry 1986; 25: 1945
- 14b Bala AE. A, Kollmann A, Ducrot PH, Majira A, Kerhoas L, Leroux P, Delorme R, Einhorn J. J. Phytopath. 2000; 148: 29
- 14c Vitrac X, Castagnino C, Waffo-Téguo P, Delaunay JC, Vercauteren J, Deffieux G, Mérillon JM. J. Agric. Food Chem. 2001; 49: 5934
- 14d Kim HJ, Saleem M, Seo SH, Jin C, Lee YS. Planta Med. 2005; 71: 973
- 14e He S, Jiang L, Wu B, Pan Y, Sun C. Biochem. Biophys. Res. Commun. 2009; 379: 283
- 15a Evans DA, Seidel D, Rueping M, Lam HW, Shaw JT, Downey CW. J. Am. Chem. Soc. 2003; 125: 12692
- 15b Kerr MS, Rovis T. J. Am. Chem. Soc. 2004; 126: 8876
- 15c Gao Y, Ren Q, Wu H, Li M, Wang J. Chem. Commun. 2010; 46: 9232
- 15d Zhu S.-F, Zhou Q.-L. Acc. Chem. Res. 2012; 45: 1365
- 15e Hashimoto T, Kawamata Y, Maruoka K. Nat. Chem. 2014; 6: 702
- 16a Misra R, Pande RC. J. Am. Chem. Soc. 1982; 104: 4471
- 16b Boger DL, Hiiter O, Mbiya K, Zhang M. J. Am. Chem. Soc. 1995; 117: 11839
- 16c Turner CD, Ciufolini MA. Beilstein J. Org. Chem. 2011; 7: 1475
- 17a Frederich JH, Harran PG. J. Am. Chem. Soc. 2013; 135: 3788
- 17b Hayakawa Y, Kawakami K, Seto H, Furihata K. Tetrahedron Lett. 1992; 33: 2701
- 18a Kobayashi J, Tsuda M, Ishibashi M. Pure Appl. Chem. 1999; 71: 1123
- 18b Kobayashi J, Watanabe D, Kawasaki N, Tsuda M. J. Org. Chem. 1997; 62: 9236
- 19a Ryan KS, Drennan CL. Chem. Biol. 2009; 16: 351
- 19b Sanchez C, Mendez C, Salas JA. Nat. Prod. Rep. 2006; 23: 1007
- 19c Nakazawa J, Yajima J, Usui T, Ueki M, Takatsuki A, Imoto M, Toyoshima YY, Osada H. Chem. Biol. 2005; 10: 131
- 19d Dhiman S, Ramasastry SS. V. Chem. Commun. 2015; 51: 557
- 19e Jordan JA, Gribble GW, Badenock JC. Tetrahedron Lett. 2011; 52: 6772
- 19f Scarpi D, Faggi C, Occhiato EG. J. Nat. Prod. 2017; 80: 2384
- 19g Munday-Finch SC, Wilkins AL, Miles CO. J. Agric. Food Chem. 1998; 46: 590
- 19h Lai E, Lepeleire ID, Crumley TM, Liu F, Wenning LA, Michiels N, Vets E, O’Neill G, Wagner JA, Gottesdiener K. Clin. Pharmacol. Ther. 2007; 81: 849
- 20a Kim H, Lantvit D, Hwang CH, Kroll DJ, Swanson SM, Franzblau SG, Orjala J. Bioorg. Med. Chem. 2012; 20: 5290
- 20b Richter JM, Ishihara Y, Masuda T, Whitefield BW, Llamas T, Pohjakallio A, Baran PS. J. Am. Chem. Soc. 2008; 130: 17938
- 21a Kong YC, Ng KH, Wat KH, Wong A, Saxena IF, Cheng KF, But PP. H, Chang HT. Planta Med. 1985; 51: 304
- 21b Chen H, Bai J, Fang Z.-F, Yu S.-S, Ma S.-G, Xu S, Li Y, Qu J, Ren J.-H, Li L. J. Nat. Prod. 2011; 74: 2438
- 22a Zhang W, Liu Z, Li S, Yang T, Zhang Q, Ma L, Tian X, Zhang H, Huang C, Zhang S, Ju J, Shen Y, Zhang C. Org. Lett. 2012; 14: 3364
- 22b Blair LM, Sperry J. Chem. Commun. 2016; 52: 800
- 23a Stevens BR, Fernandez A, Martinez del Rio C. J. Exp. Biol. 1988; 135: 1
- 23b Gomez C, Berteina-Raboin S, Nanteuil GD, Guillaumet G. Bioorg. Med. Chem. 2013; 21: 7216
- 23c Sanchez M, McManus OB. Neuropharmacology 1996; 35: 963
- 23d George DT, Kuenstner EJ, Pronin SV. J. Am. Chem. Soc. 2015; 137: 15410
- 23e When PM, Bois JD. Angew. Chem. Int. Ed. 2009; 48: 3802
- 23f Dickson DP, Wardrop DJ. Org. Lett. 2009; 11: 1341
- 23g Trost BM, Dong G. Chem. Eur. J. 2009; 15: 6910
- 23h Yoganathan K, Rossant C, Glover RP, Cao S, Vittal JJ, Ng S, Huang Y, Buss AD, Butler MS. J. Nat. Prod. 2004; 67: 1681
- 23i Luo Q, Wei X.-Y, Yan J, Luo J.-F, Liang R, Tu Z.-C, Cheng Y.-X. J. Nat. Prod. 2017; 80: 61
- 23j Verma K, Taily IM, Banerjee P. Org. Biomol. Chem. 2019; 17: 8149
- 23k Chen P, Wang J, Liu K, Li C. J. Org. Chem. 2008; 73: 339
- 23l Chen H, Zhang J, Ren J, Wang W, Xiong W, Zhang Y, Bao L, Liu H. Chem. Biodivers. 2018; 15: e1700567
- 23m Ota K, Kurokawa T, Kawashima E, Miyaoka H. Mar. Drugs 2009; 7: 654
- 23n Zhang L.-H, Feng B.-M, Chen G, Li S.-G, Sun Y, Wu H.-H, Bai J, Hua H.-M, Wang H.-F, Pei Y.-H. RSC Adv. 2016; 6: 42361
- 23o McGee P, Betournay G, Barabe F, Barriault L. Angew. Chem. Int. Ed. 2017; 56: 6280
- 23p Yen C.-F, Liao C.-C. Angew. Chem. Int. Ed. 2002; 41: 4090
- 23q Beaulieu R, Grand E, Stasik I, Attoumbré J, Chesnais Q, Gobert V, Ameline A, Giordanengod P, Kovenskya J. Pest Manage. Sci. 2019; 75: 793
- 23r Nikolic NC, Stankovic MZ. J. Agric. Food Chem. 2003; 51: 1845
- 23s Corey EJ, Pearce HL. J. Am. Chem. Soc. 1979; 101: 5841
- 23t Miyashita M, Suzuki T, Yoshikoshi A. J. Am. Chem. Soc. 1989; 111: 3728
- 23u Liu J, Chen S, Li N, Qiua FG. Adv. Synth. Catal. 2019; 361: 3514
- 23v Lin K.-W, Ananthan B, Tseng S.-F, Yan T.-H. Org. Lett. 2015; 17: 3938
- 23w Blodgett JA. V, Oh DC, Cao SG, Currie CR, Kolter R, Clardy J. Proc. Natl. Acad. Sci. U.S.A. 2010; 107: 11692
- 23x Fisch KM. RSC Adv. 2013; 3: 18228
- 23y Mercado-Marin EV, Garcia-Reynaga P, Romminger S, Pimenta EF, Romney DK, Lodewyk MW, Williams DE, Andersen RJ, Miller SJ, Tantillo DJ, Berlinck RG. S, Sarpong R. Nature 2014; 509: 318
- 23z Unsworth WP, Cuthbertson JD, Taylor RJ. K. Org. Lett. 2013; 15: 3306
- 23aa Williams RM, Cox RJ. Acc. Chem. Res. 2003; 36: 127
- 23ab Komori K, Taniguchi T, Mizutani S, Monde K, Kuramochi K, Tsubaki K. Org. Lett. 2014; 16: 1386
- 23ac Jo D, Han S. Org. Chem. Front. 2017; 4: 506
- 23ad Onishi T, Sebahar PR, Williams RM. Org. Lett. 2003; 5: 3135
- 23ae Edmondson SD, Danishefsky SJ. Angew. Chem. Int. Ed. 1998; 37: 1138
- 23af Fukuyama T, Yang L. J. Am. Chem. Soc. 1989; 111: 8303
- 23ag Zheng Z, Touve M, Barnes J, Reich N, Zhang L. Angew. Chem. Int. Ed. 2014; 53: 9302
- 23ah Li H, Fu B, Wang MA, Li N, Liu WJ, Xie ZQ, Ma YQ, Qin Z. Eur. J. Org. Chem. 2008; 1753
- 23ai Malona JA, Cariou K, Frontier AJ. J. Am. Chem. Soc. 2009; 131: 7560
- 23aj Paquette LA, Borrelly S. J. Org. Chem. 1995; 60: 6912
- 23ak Borrelly S, Paquette LA. J. Am. Chem. Soc. 1996; 118: 727
- 23al Selig P, Herdtweck E, Bach T. Chem. Eur. J. 2009; 15: 3509
- 23am Selig P, Bach T. Angew. Chem. Int. Ed. 2008; 47: 5082
- 23an Denmark SE, Cottell JJ. Adv. Synth. Catal. 2006; 348: 2397
- 23ao Bernauer K, Englert G, Vetter W, Weiss EK. Helv. Chim. Acta 1969; 52: 1886
- 23ap Zhang H, Curran DP. J. Am. Chem. Soc. 2011; 133: 10376
- 23aq Zhang BX, Zhang J, Tan Y, Liu Q, Liu M. Molecules 2012; 17: 9641
- 23ar Chattopadhyay AK, Ly VL, Jakkepally S, Berger G, Hanessian S. Angew. Chem. Int. Ed. 2016; 55: 2577
- 23as Hugelshofer CL, Palani V, Sarpong R. J. Am. Chem. Soc. 2019; 141: 8431
- 23at Dethe DH, Kumar VB. Org. Chem. Front. 2015; 2: 548
- 23au Gribble GW. Pure Appl. Chem. 2003; 75: 1417
- 23av Scarpi D, Faggi C, Occhiato EG. J. Nat. Prod. 2017; 80: 2384
- 23aw Ouyang Y, Koike K, Ohmoto T. Phytochemistry 1994; 36: 1543
- 23ax Bharati AK, Singh HB. NeBIO 2012; 3: 26
- 23ay Chen H, Bai J, Fang ZF, Yu SS, Ma SG, Xu S, Li Y, Qu J, Ren JH, Li L, Si YK, Chen XG. J. Nat. Prod. 2011; 74: 2438
- 23az Li J, Zhang W, Zhang F, Chen Y, Li A. J. Am. Chem. Soc. 2017; 139: 14893
- 23ba Chiyoda K, Shimokawa J, Fukuyama T. Angew. Chem. Int. Ed. 2012; 51: 2505
- 23bb Cai SL, Song R, Dong HQ, Lin GQ, Sun XW. Org. Lett. 2016; 18: 1996
- 23bc Morris BD, Prinsep MR. J. Nat. Prod. 1999; 62: 688
- 23bd Tang M.-L, Peng P, Liu Z.-Y, Zhang J, Yu J.-M, Sun X. Chem. Eur. J. 2016; 22: 14535
- 23be He S, Jiang L, Wu B, Pan Y, Sun C. Biochem. Biophys. Res. Commun. 2009; 379: 283
- 23bf Xi Y.-K, Zhang H, Li R.-X, Kang S.-Y, Li J, Li Y. Chem. Eur. J. 2019; 25: 3005
- 23bg Marti C, Carreira EM. J. Am. Chem. Soc. 2005; 127: 11505
- 23bh Ishikawa M, Ninomiya T. J. Antibiot. 2008; 61: 692
- 23bi Hayashi Y, Shoji M, Yamaguchi S, Mukaiyama T, Yamaguchi J, Kakeya H, Osada H. Org. Lett. 2003; 5: 2287
- 23bj Beutler JA, Hilton BD, Clark P, Tempesta MS, Corley DG. J. Nat. Prod. 1988; 51: 562
- 23bk Mizuno H, Domon K, Masuya K, Tanino K, Kuwajima I. J. Org. Chem. 1999; 64: 2648
- 23bl Mehta G, Reddy AV, Murthy AN, Reddy DS. J. Chem. Soc., Chem. Commun. 1982; 540
- 23bm Wang J.-C, Krische MJ. Angew. Chem. Int. Ed. 2003; 42: 5855
- 23bn Hudlicky T, Kutchan TM, Wilson SR, Mao DT. J. Am. Chem. Soc. 1980; 102: 6351
- 23bo Hellwig V, Dasenbrock J, Schumann S, Steglich W, Leonhardt K, Anke T. Eur. J. Org. Chem. 1998; 73
- 23bp Srikrishna A, Dethe DH. Org. Lett. 2003; 5: 2295
- 23bq Mehta G, Murthy AS. K. Tetrahedron Lett. 2003; 44: 5243
- 23br Yang F, Chen WD, Deng R, Zhang H, Tang J, Wu KW, Li DD, Feng GK, Lan WJ, Li HJ, Zhu XF. J. Transl. Med. 2013; 11: 32
- 23bs Yang F, Chen WD, Deng R, Li DD, Wu KW, Feng GK, Li HJ, Zhu XF. J. Pharmacol. Sci. 2012; 119: 214
- 23bt Li H.-J, Lan W.-J, Lam C.-K, Yang F, Zhu X.-F. Chem. Biodivers. 2011; 8: 317
- 23bu Mehta G, Pallavi K. Tetrahedron Lett. 2006; 47: 8355
- 23bv Guo L, Frey W, Plietker B. Org. Lett. 2018; 20: 4328
- 23bw Weyerstahl P, Marschall H, Seelmann I, Jakupovic J. Eur. J. Org. Chem. 1998; 1205
- 23bx Davis CE, Duffy BC, Coates RM. Org. Lett. 2000; 2: 2717
- 23by Paquette LA, Okazaki ME, Caille JC. J. Org. Chem. 1988; 53: 477
- 23bz Kim Y.-J, Yoon Y, Lee H.-Y. Tetrahedron 2013; 69: 7810
- 23ca Paquette LA, Doherty AM. Synthesis of Nonpolycyclopentanoid Natural Products by Way of Diquinane Intermediates . In Polyquinane Chemistry: Syntheses and Reactions, Reactivity and Structure: Concepts in Organic Chemistry 26, Paquette, L. A.; Doherty, A. M., Ed. Springer-Verlag; Berlin: 1987: 112-126
- 23cb Paquette LA, Doherty AM. Synthesis of Diquinane Natural Products . In Polyquinane Chemistry: Syntheses and Reactions, Reactivity and Structure: Concepts in Organic Chemistry 26, Paquette, L. A.; Doherty, A. M., Ed. Springer-Verlag; Berlin: 1987: 127-168
- 23cc Hou S.-H, Tu Y.-Q, Wang S.-H, Xi C.-C, Zhang F.-M, Wang S.-H, Li Y.-T, Liu L. Angew. Chem. Int. Ed. 2016; 55: 4456
- 23cd Li F, Tartakoff SS, Castle SL. J. Am. Chem. Soc. 2009; 131: 6674
- 23ce King SM, Calandra NA, Herzon SB. Angew. Chem. Int. Ed. 2013; 52: 3642
- 23cf Zhang J, Wang X, Li S, Li D, Liu S, Lan Y, Gong J, Yang Z. Chem. Eur. J. 2015; 21: 12596
- 23cg Sugawara H, Kasuya A, Iiataka Y, Shibata S. Chem. Pharm. Bull. 1991; 39: 3051
- 23ch Zhang W, Liu Z, Li S, Yang T, Zhang Q, Ma L, Tian X, Zhang H, Huang C, Zhang S, Ju J, Shen Y, Zhang C. Org. Lett. 2012; 14: 3364
- 23ci Blaira LM, Sperry J. Chem. Commun. 2016; 52: 800
- 23cj Qiu Y, Lan W.-J, Li H.-J, Chen L.-P. Molecules 2018; 23: 2095
- 23ck Liu W, Wang B. Chem. Eur. J. 2018; 24: 16511
- 23cl Mehta G, Singh SR. Angew. Chem. Int. Ed. 2006; 45: 953
- 23cm Shi L, Meyer K, Greaney MF. Angew. Chem. 2010; 122: 9436
- 24a Sun L.-L, Deng C.-L, Tang R.-Y, Zhang X.-G. J. Org. Chem. 2011; 76: 7546
- 24b Satpathi B, Dhiman S, Ramasastry SS. V. Eur. J. Org. Chem. 2014; 2022
- 24c Capodilupo AL, Fabiano E, Marco LD, Ciccarella G, Gigli G, Martinelli C, Cardone A. J. Org. Chem. 2016; 81: 3235
- 24d Kotha S, Chavan AS, Goyal D. ACS Comb. Sci. 2015; 17: 253
- 24e Kotha S, Ghosh A. Tetrahedron 2004; 60: 10833
- 24f Kotha S, Banerjee S. RSC Adv. 2013; 3: 7642
- 24g Kotha S, Krishna NG, Halder S, Misra S. Org. Biomol. Chem. 2011; 9: 5597
- 24h Kotha S, Sreenivasachary N, Mohanraja K, Durani S. Bioorg. Med. Chem. Lett. 2001; 11: 1421
- 24i Kotha S, Lahiri K. Synlett 2007; 2767
- 24j Kotha S, Meshram M, Aswar VR. Tetrahedron Lett. 2019; 60: 151337
- 24k Kotha S, Halder S, Bramachary E, Ganesh T. Synlett 2000; 853
- 24l Kotha S, Chavan AS, Goyal D. ACS Omega 2019; 4: 22261
- 24m Kotha S, Chandravathi C. Chem. Rec. 2017; 17: 1039
- 25a Kotha S, Cheekatla SR. ChemistrySelect 2017; 2: 6877
- 25b Marchand AP, Dave PR. J. Org. Chem. 1989; 54: 2775
- 25c Chupakhin E, Babich O, Prosekov A, Asyakina L, Krasavin M. Molecules 2019; 24: 4165
- 25d Kotha S, Manivannan E, Ganesh T, Sreenivasachary N, Deb A. Synlett 1999; 1618
- 25e Kotha S, Manivannan E. ARKIVOC 2003; (iii): 67
- 26 Kotha S, Ali R. Tetrahedron 2015; 71: 1597
- 27 Kotha S, Cheekatla SR, Fatma A. ACS Omega 2019; 4: 17109
- 28a Kotha S, Ali R, Panguluri NR, Deb AC. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2018; 57: 1489
- 28b Kotha S, Meshram M, Chakkapalli C. Beilstein J. Org. Chem. 2018; 14: 2468
- 28c Kotha S, Ali R, Panguluri NR, Datta A, Kannaujiya KK. Tetrahedron Lett. 2018; 59: 4080
- 29a Kotha S, Halder S. Synlett 2010; 337
- 29b Kotha S, Halder S, Damodharan L, Pattabhi V. Bioorg. Med. Chem. Lett. 2002; 12: 1113
- 29c Kotha S, Ganesh T, Ghosh AK. Bioorg. Med. Chem. Lett. 2000; 10: 1755
- 29d Kotha S, Ali R. Tetrahedron 2015; 71: 6944
- 30a Kotha S, Ali R, Tiwari A. Synlett 2013; 24: 1921
- 30b Kotha S, Ali R, Tiwari A. Synthesis 2014; 46: 2471
- 31a Kotha S, Manivannan E. J. Chem. Soc., Perkin Trans. 1 2001; 2543
- 31b Kotha S, Sreevani G. Tetrahedron Lett. 2015; 56: 5903
- 32a Kotha S, Deb AC, Chattopadhyay S. Lett. Org. Chem. 2006; 3: 39
- 32b Yoshida K, Itatsu Y, Fujino Y, Inoue H, Takao K.-I. Angew. Chem. Int. Ed. 2016; 55: 6734; Angew. Chem. 2016, 128, 6846
-
33 Kotha, S.; Keesari, R. R (unpublished results)
- 34 Kotha S, Ali R. Heterocycles 2015; 90: 645
- 35 Kotha S, Ali R. J. Chem. Sci. 2019; 131: 66
- 36 Kotha S, Mandal K, Tiwari A, Mobin SM. Chem. Eur. J. 2006; 12: 8024
- 37a Kotha S, Sreevani G. Eur. J. Org. Chem. 2018; 5935
- 37b Kotha S, Sreevani G, Dzhemileva LU, Yunusbaeva MM, Dzhemilev UM, D’yakonov VA. Beilstein J. Org. Chem. 2019; 15: 2774
- 38a Zhou F, Liu Y.-L, Zhou J. Adv. Synth. Catal. 2010; 352: 1381
- 38b Antonchick AP, Gerding-Reimers C, Catarinella M, Schürmann M, Preut H, Ziegler S, Rauh D, Waldmann H. Nat. Chem. 2010; 2: 735
- 38c Panda SS, Jones RA, Bachawala P, Mohapatra PP. Med. Chem. 2017; 17: 1515
- 38d Barnett DS, Guy RK. Chem. Rev. 2014; 114: 11221
- 38e Miyake FY, Yakushijin K, Horne DA. Org. Lett. 2004; 6: 711
- 38f Onishi T, Sebahar PR, Williams RM. Org. Lett. 2003; 5: 3135
- 39 Kotha S, Ali R. Tetrahedron Lett. 2015; 56: 3992
- 40 Kotha S, Sreevani G. Tetrahedron Lett. 2018; 59: 1996
- 41 Kotha S, Dipak MK, Mobin SM. Tetrahedron 2011; 67: 4616
- 42a Kotha S, Deb AC. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2008; 47: 1120
- 42b Kotha S, Krishna NG, Halder S, Misra S. Org. Biomol. Chem. 2011; 9: 5597
- 42c Kotha S, Panguluri NR, Ali R. Eur. J. Org. Chem. 2017; 5316
- 43a Penning TD, Talley JJ, Bertenshaw SR, Carter JS, Collins PW, Docter S, Graneto MJ, Lee LF, Malecha JW, Miyashiro JM. J. Med. Chem. 1997; 40: 1347
- 43b Wasylyk C, Zheng H, Castell C, Debussche L, Multon M.-C, Wasylyk B. Cancer Res. 2008; 68: 1275
- 43c Ivachtchenko AV, Dmitriev DE, Golovina ES, Kadieva MG, Koryakova AG, Kysil VM, Mitkin OD, Okun IM, Tkachenko SE, Vorobiev AA. J. Med. Chem. 2010; 53: 5186
- 43d Ivachtchenko AV, Golovina ES, Kadieva MG, Kysil VM, Mitkin OD, Vorobiev AA, Okun I. Bioorg. Med. Chem. Lett. 2012; 22: 4273
- 43e Zheng P.-F, Zeng R, Jiang K, Li H.-W, Ye Y, Mu C, Shuai L, Ouyang Q, Chen Y.-C. Org. Lett. 2019; 21: 10052
- 44a Kotha S, Deb AC. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2008; 47: 1120
- 44b Kotha S, Deb AC, Kumar RV. Bioorg. Med. Chem. Lett. 2005; 15: 1039
- 44c Kesharwani S, Sahu NK, Kohli DV. Pharm. Chem. J. 2009; 43: 315
- 44d Singh P, Paul K. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2006; 45: 247
- 45a Bartlett PD, Goldstein IS. J. Am. Chem. Soc. 1947; 69: 2553
- 45b Cox O, Rivera LA. Synth. Commun. 1978; 8: 261
- 46 Kotha S, Kubiak G, Lannoye G, Cook JM. J. Org. Chem. 1988; 53: 5173
- 47 Kotha S, Cook JM. Org. Prep. Proced. Int. 1990; 22: 630
- 48a Ito H, Hasegawa M, Takenaka Y, Kobayashi T, Iguchi K. J. Am. Chem. Soc. 2004; 126: 4520
- 48b Iwashima M, Terada I, Okamoto K, Iguchi K. J. Org. Chem. 2002; 67: 2977
- 48c Ito H, Kobayashi T, Hasegawa M, Iguchi K. Tetrahedron Lett. 2003; 44: 1259
-
49 Kotha, S.; Pulletikurti, S. (unpublished results)
- 50 Kotha S, Chinnam AK. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2017; 56: 1065
- 51 Kotha S, Ravikumar O. Eur. J. Org. Chem. 2014; 5582
- 52a Blunt JW, Copp BR, Keyzers RA, Munro MH, Prinsep MR. Nat. Prod. Rep. 2016; 33: 382
- 52b Carreira EM, Fessard TC. Chem. Rev. 2014; 114: 8257
- 52c Ferrari FD, Pasqua AE, Ledgard AJ, Marquez R. Org. Biomol. Chem. 2013; 11: 3469
- 52d Ammann SE, Rice GT, White MC. J. Am. Chem. Soc. 2014; 136: 10834
- 53a Moriarty RM, Duncan MP, Vaid RK, Prakash O. Org. Synth. 1990; 68: 175
- 53b Sivakumar R. Ph. D. Thesis . IIT Bombay; India: 2001
- 54 Kotha S, Ali R. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2016; 55: 1099
- 55a Bertz SH, Cook JM, Gawish A, Weiss U. Org. Synth. 1986; 64: 27
- 55b Wrobel J, Takahashi K, Honkan V, Lannoye G, Cook JM. J. Org. Chem. 1983; 48: 139
- 55c Deshpande MN, Jawdosiuk M, Kubiak G, Venkatachalam M, Weiss U, Cook JM. J. Am. Chem. Soc. 1985; 107: 4786
- 55d Fu X, Cook JM. J. Org. Chem. 1992; 57: 5121
- 55e Fu X, Cook JM. Aldrichimica Acta 1992; 25: 43
- 55f Gupta AK, Fu X, Snyder JP, Cook JM. Tetrahedron 1991; 47: 3665
- 55g Weiss U, Edwards JM. Tetrahedron Lett. 1968; 4885
- 56 Kotha S, Ravikumar O. Tetrahedron Lett. 2014; 55: 5781
- 57 Kotha S, Gunta R. J. Org. Chem. 2017; 82: 8527
- 58a Kreis LM, Carreira EM. Angew. Chem. Int. Ed. 2012; 51: 3436
- 58b Roush WR. J. Am. Chem. Soc. 1980; 102: 1390
- 58c Inubushi Y, Naksno J. Tetrahedron Lett. 1965; 31: 2723
- 58d Kotha S, Pulletikurti S. Synthesis 2019; 51: 3981
- 59a Lai W.-Y, Xia R, He Q.-Y, Levermore PA, Huang W, Bradley DD. C. Adv. Mater. 2009; 21: 355
- 59b Shang H, Fan H, Liu Y, Hu W, Li Y, Zhan X. Adv. Mater. 2011; 23: 1554
- 59c Burk MJ, Harlow RL. Angew. Chem., Int. Ed. Engl. 1990; 29: 1462 Angew. Chem. 1990, 102, 1511
- 59d Hoang MH, Cho MJ, Kim DC, Kim KH, Shin JW, Cho MY, Joo J.-S, Choi DH. Org. Electron. 2009; 10: 607
- 60 Kotha S, Todeti S, Aswar VR. Beilstein J. Org. Chem. 2018; 14: 2537
- 61 Kotha S, Pulletikurti S. Heterocycles 2019; 101: 717
- 62a Simpkins N. In Sulfones in Organic Synthesis . Baldwin JE, Magnus PD. Pergamon Press; Oxford: 1993
- 62b Barbuceanu SF, Almajan GL, Saramet I, Draghici C, Tarcomnicu AI, Bancescu G. Eur. J. Med. Chem. 2009; 44: 4752
- 62c van der Westhuyzen R, Strauss E. J. Am. Chem. Soc. 2010; 132: 12853
- 62d Ivashchenko AV, Golovina ES, Kadieva MG, Kysil VM, Mitkin OD, Okun IM. Pharm. Chem. J. 2012; 46: 406
- 62e Tfelt-Hansen P, De Vries P, Saxena PR. Drugs 2000; 60: 1259
- 63a Zhang M, Flynn DL, Hanson PR. J. Org. Chem. 2007; 72: 3194
- 63b Kotha S, Gunta R. Beilstein J. Org. Chem. 2015; 11: 1373
- 64 Mehta G, Kotha S, Marchand AP, Kaya R. J. Org. Chem. 1984; 49: 3848
- 65 Mehta G, Kotha S. J. Org. Chem. 1985; 50: 5537
- 66 Mehta G, Kotha S. Tetrahedron Lett. 1983; 24: 809
- 67 Mehta G, Srikrishna A, Kotha S, Reddy KR. J. Org. Chem. 1987; 52: 457
- 68 Kotha S, Manivannamn E. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2002; 41: 808
- 69a Kotha S, Cheekatla SR, Meshram M, Bandi V, Seema V. Asian J. Org. Chem. 2019; 8: 2097
-
69b Kotha S., Cheekatla S. R.; Indian J. Chem.; 2020, accepted
- 70 Kotha S, Seema V, Singh K, Deodhar KD. Tetrahedron Lett. 2010; 51: 2301
- 71a Dols PP. M. A, Klunder AJ. H, Zwanenburg BA. Tetrahedron Lett. 1993; 34: 3181
- 71b Cookson RC, Henstock J, Hudec J. J. Am. Chem. Soc. 1966; 88: 1059
- 72 Kotha S, Keesari RR, Fatma A, Gunta R. J. Org. Chem. 2020; 85: 851
- 73 Kotha S, Keesari RR, Ansari S. Synthesis 2019; 51: 3989
- 74a Iwata C, Takemoto Y, Doi M, Imanishi T. J. Org. Chem. 1988; 53: 1623
- 74b Paquette LA, Meister PG, Friedrich D, Sauer DR. J. Am. Chem. Soc. 1993; 115: 49
- 74c Davis CE, Duffy BC, Coates RM. Org. Lett. 2000; 2: 2717
- 74d Schmidt AW, Olpp T, Schmid S, Jager A, Knolker H.-J. Tetrahedron 2009; 65: 5484
- 75 Gupta K, Kotha S, Opansky B, Cook JM. J. Org. Chem. 1990; 55: 4480
- 76 Kotha S, Ali R, Srinivas V, Krishna NG. Tetrahedron 2015; 71: 129
- 77 Kotha S, Ali R. Tetrahedron Lett. 2015; 56: 2172
- 78 Kotha S, Aswar VR. Org. Lett. 2016; 18: 1808
- 79 Lannoye G, Kotha S, Wehrli S, Cook JM. J. Org. Chem. 1988; 53: 2327
- 80a Kotha S, Brahmachary E, Sivakumar R, Joseph A, Sreenivssachary N. Tetrahedron Lett. 1997; 38: 4497
- 80b Kotha S, Sivakumar R. ARKIVOC 2005; (xi): 78
- 80c Hudlicky T, Reed JW. The Way of Synthesis: Evolution of Design and Methods for Natural Products. Wiley-VCH; Weinheim: 2007: 95
- 81a Kotha S, Chinnam AK, Tiwari A. Beilstein J. Org. Chem. 2013; 9: 2709
-
81b
Kotha S,
Chinnam AK.
Synthesis 2014; 46: 301
- 82 Kotha S, Hollinshead S, Grubisha D, Laib F, Bennett D, Cook JM. J. Org. Chem. 1990; 55: 3858
- 83 Kotha S, Ali R, Chinnam AK. Tetrahedron Lett. 2014; 55: 4492
- 84 Mehta G, Kotha S, Bhadbhade MM, Venkateshan K. J. Chem. Soc., Chem. Commun. 1981; 755
- 85 Kotha S, Sivakumar R, Damodharan L, Pattabhi V. Tetrahedron Lett. 2002; 43: 4523
- 86 Kotha S, Rallapalli S. ARKIVOC 2010; (iv): 90
- 87 Kotha S, Chinnam AK, Ali R. Beilstein J. Org. Chem. 2015; 11: 1123
- 88 Kotha S, Chinnam AK. Heterocycles 2015; 90: 690
- 89 Kotha S, Sivakumar R. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2016; 55: 1107
- 90 Kotha S, Cheekatla SR, Chinnam AK, Jain T. Tetrahedron Lett. 2016; 57: 5605
Paxilline and Emindole SB:
Agelastatin A:
Variecolol:
Spiroapplanatumine K:
Laurentristich-4-ol:
Xestenone:
Sporulaminal A:
Magellanine:
Solanidine:
Picrotoxinin:
Paniculatine:
Frontalamide A and B:
Cyclopiamine A and B:
Spirobacillene B:
Brevianamide A:
Berkeleyamide D:
Spirotryprostatin A:
Mitomycin C:
Rocaglamide:
Kalmanol:
Meloscine:
Scandine:
Epimeloscine:
Deoxycalyciphylline B:
Isodaphlongamine H:
Daphlongamine H:
Bruceolline J:
Bruceolline I:
Longeracinphyllins A:
Amathaspiramide B:
Pallidol:
Spirotryprostatin A and B:
Pseurotin A:
Erythroskyrin:
(–)-Coriolin:
(+)-Hirsutene:
Cucumins A–D:
Pleurotellol:
Hirsutanol A:
Hirsutanol E:
Dichomitol:
Dendroxine:
(±)-Cameroonanol, isocomene, silphinene, (–)-silphiperfol-6-ene, modhephen-2-ene and modhephenol:
Laurenene:
Pentalenene:
Cantabrenonic acid:
Conidiogenol, conidiogenone and conidiogenone B:
(–)-Acutumine:
Retigeranic acids A and B:
Spiroindimicin B, C and D:
For linear triquinanes:
Merrilactone A:
Anislactones A: