个人简介
Professor West was born and raised in southern Arizona, and received his undergraduate training (Chemistry, with Honors and Summa cum Laude) at the University of Arizona in Tucson. While there, he performed research with Victor Hruby on conformationally restricted analogues of the peptide hormone oxytocin, and developed one of the first HPLC-based methods for amino acid analysis of peptide hydrolysates (publication 1). He then moved to Madison, Wisconsin where he was an NSF Predoctoral Fellow at the University of Wisconsin in the labs of Professor Edwin Vedejs. His doctoral research concerned the generation of nonstabilized azomethine ylides using desilylation methods its application to the synthesis of pyrrolizidine alkaloids (publications 2-3). He spent two years at Columbia University as an NIH Postdoctoral Fellow with Professor Gilbert Stork, working on radical cyclization-based approaches to the cardenolides (publication 23).
Professor West began his independent career at the University of Utah in 1988. Initially, his program focused on the use of pyran-4-one photochemistry for the rapid assembly of complex polycyclic skeletons, and the Stevens rearrangement of metallocarbene-derived ylides. Subsequent areas of interest have included the Nazarov cyclization, taxane synthesis and bioconjugate chemistry. (See the research description for a more detailed discussion of current research interests.) In 2002, Professor West moved to the University of Alberta in Edmonton, where he is currently Professor of Chemistry and Associate Chair (Research) of the department.
Awards and Honours
2012-2013 Teacher of the Year Award, University of Alberta Chemistry Students’ Association
2011 Alfred Bader Award, Canadian Society for Chemistry
2009 Faculty of Science Award for Excellent Teaching, University of Alberta
2005-2006 Chemistry Students’ Association Award for Excellence in Teaching, University of Alberta
2004-2005 Chemistry Students’ Association Award for Teaching Excellence, University of Alberta
1998-1999 University Professor, University of Utah
1994-1995 American Cyanamid Faculty Award
1993-1994 Eli Lilly Grantee
1992 Robert W. Parry Teaching Award, Department of Chemistry, University of Utah
1991-1994 American Cancer Society Junior Faculty Research Award
1990 Chemistry SAC Award for Excellence in Undergraduate Teaching, University of Utah
1986-1988 National Institutes of Health Postdoctoral Fellowship, Columbia University
1981-1984 National Science Foundation Predoctoral Fellowship, University of Wisconsin-Madison
1980-1981 Samuel M. McElvain Distinguished Teaching/Research Assistantship, University of Wisconsin
1979-1980 Tartarian Scholarship, University of Arizona
1979 Dreyfus Summer Scholar Fellowship, University of Chicago
1976-1978 Robert Nugent Scholarship, University of Arizona
研究领域
The activities of my research group are centered on various aspects of chemical synthesis. Synthesis provides access to otherwise unavailable compounds for asking important research questions concerning topics ranging from biology to catalysis to basic chemical reactivity. Our interests can be divided into three main areas: (1) novel strategies for the efficient construction of complex natural products; (2) new methodology based on unusual reactive intermediates; and (3) de novo design of bioactive small molecules with unique binding or transport properties. Students in my group become proficient in diverse synthetic methodology and spectroscopic techniques in the course of pursuing their research, and are exposed to wider scientific horizons as a consequence of their interactions with others in the group as well as our collaborators. Some of our current projects are listed below.
New Approaches to the Taxane Skeleton: We have developed an efficient entry to functionalised taxane AB or ABC ring systems (Fig. 1) utilizing stereoselective Nazarov cyclization of dienones such as 1, followed by a later oxidative fragmentation to unveil the 8-membered B-ring. We are currently focusing on converting these intermediates into structural analogues of the potential MDR reversal agent taxinine, and also exploring second-generation approaches to further streamline the route
A related project involves the development of new methodology based upon domino processes initiated by the Nazarov reaction.
Ammonium Ylide Rearrangements for the Synthesis of Alkaloids: Previous work in our labs has shown that polycyclic amine structures found in many classes of alkaloids can be easily accessed via metallocarbene-derived ammonium ylides. A current focus in our group is the ergot alkaloid class, as exemplified by lysergic acid (Fig. 2). Dizaoketones, when treated with transition metal catalysts, generate transient metallocarbenes. If there is a nearby basic amine, ring-closure to an intermediate ammonium ylide ensues, followed by rearrangement to give a substituted heterocycle. Analogous chemistry with oxonium ylides is being applied to the synthesis of the tumor promoter phorbol.
Photochemical [4 + 4]-Cycloadditions for Synthesis of Cyclooctanoid Natural Products: Pyran-2-ones with pendant 1,3-dienes can undergo efficient intramolecular [4 + 4]-cycloaddition when they are irradiated with long-wavelength UV light. This reaction is being used as the key transformation in approaches to the chemical synthesis of the terpenoid natural product traversianal (Fig 3). Similar chemistry is being applied to the synthesis of 7,8-epoxy-4-basmen-6-one.[No text in field]
近期论文
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Reactivity and Stereoselectivity of 6π and Nazarov Electrocyclizations of Bridged Bicyclic Trienes and Divinyl Ketones. Ashay Patel, F. G. West, and K. N. Houk. J. Org. Chem., 2015, 80 (5), pp 2790–2795 (pdf)
“Experimental and Computational Studies on Interrupted Nazarov Reactions: Exploration of Umpolung Reactivity at the α-Carbon of Cyclopentanones,” Yen-Ku Wu, Christine R. Dunbar, Robert McDonald, Michael J. Ferguson and F. G. West, J. Am. Chem. Soc. 2014, 136, pp 14903-14911 (pdf)
“Azide trapping of metallocarbenes: generation of reactive C-acylimines and domino trapping with nucleophile,” Tina M. Bott, Bren Jordan Atienza and F. G. West, RSC Adv., 2014, 4, 31955–31959 (pdf)
“Automated synthesis and dosimetry of 6-deoxy-6-[18F]fluoro-D-fructose (6-[18F]FDF): a radiotracer for imaging of GLUT5 in breast cancer ,“ Vincent Bouvet, Hans S Jans, Melinda Wuest, Olivier-Mohamad Soueidan, John Mercer, Alexander JB McEwan, Frederick G West, Chris I Cheeseman, Frank Wuest, Am. J. Nucl. Med. Mol. Imaging 2014, 4, 248–259 (pdf)
“Formal Homologous Aldol Reactions: Interrupting the Nazarov Cyclization via Carboalkoxylation of Alkynes,” Yen-Ku Wu and F. G. West, Org. Lett. 2014, 16, 2534–2537 (pdf)
“α-Hydroxycyclopentanones via one-pot oxidation of the trimethylaluminum-mediated Nazarov reaction with Triplet Oxygen,” Yonghoon Kwon, Owen Scadeng, Robert McDonald, F. G. West, Chem. Commun., 2014, 50, 5558-5560. (pdf)
“Ready Access to Alkylidenecyclopentenones by Nazarov Cyclization/β-Elimination of 2-Hydroxyalkyl-1,4-dien-3-ones,” Owen Scadeng, F. G. West, Eur. J. Org. Chem. 2014, 1860-1865. (pdf)
“Efficient synthesis of bicyclo[6.3.0]undecadienes by Nazarov cyclization/regioselective elimination,” Carson D. Matier, Yonghoon Kwon, F. G. West, Can. J. Chem. 2014, 92. 58-61. (pdf)
“Hydroxylic additives enhance yield and scalability of silicon-directed Nazarov reaction,” Shaon Joy, Waka Nakanishi, F. G. West, Tetrahedron Lett. 2013, 54, 5573-5576. (pdf)
“Organoaluminum-Mediated Interrupted Nazarov Reaction,” Yonghoon Kwon, Robert McDonald, F. G. West, Angew. Chem. Int. Ed. 2013, 52, 8616-8619. (pdf)
“Nazarov Reactions of Vinyl Cyclopropylamines: An Approach to the Imino-Nazarov Problem,” Sara A. Bonderoff , Tina N. Grant , F. G. West *, and Martin Tremblay, Org. Lett. 2013, 15, 2888-2891. (pdf)
“Regioselective Synthesis of 2-Iminooxazinones from Dioxinones and Carbodiimides,” Jeffrey R. Johnston, F. G. West, Tetrahedron Lett. 2012, 53, 5479-5482. (pdf)
“Construction of α-Amido-indanones via Formal Allenamide Hydroacylation/Nazarov Cyclization,” Yen-Ku Wu, Tianmin Niu, F. G. West, Chem. Commun. 2012, 48, 9186-9188. (pdf)
“Prion Inhibition with Multivalent PrPSc Binding Compounds," Charles E. Mays, Shaon Joy, Lei Li, Linghui Yu, Sacha Genovesi, Frederick G. West, David Westaway, Biomaterials 2012, 33, 6808-6822. (pdf)
“Superacid Catalyzed Friedel-Crafts Cyclization of Unactivated Alkenes," Sara A. Bonderoff, F. G. West, Martin Tremblay, Tetrahedron Lett. 2012, 53, 4600-4603. (pdf)
“Homologous Mukaiyama Reactions via Trapping of the Nazarov Intermediate with Silyloxyalkenes," Yen-Ku Wu, Robert McDonald, F. G. West, Org. Lett. 2011, 13, 3584-3587. (pdf)
"Radiopharmacological Evaluation of 6-Deoxy-6-[18F]fluoro-d-fructose as a Radiotracer for PET Imaging of GLUT5 in Breast Cancer," Melinda Wuest, Brendan J. Trayner, Tina N. Grant, Hans-Soenke Jans, John R. Mercer, David Murray, Frederick G. West, Alexander J. B. McEwan, Frank Wuest, Chris I. Cheeseman, Nucl. Med. Biol. 2011, 38, 461-475. (pdf)
"Expedient Route to the Tigliane-Daphnane Skeleton via Oxonium Ylide [1,2]-Shift," Craig Stewart, Robert McDonald, F. G. West, Org. Lett. 2011, 13, 720-723. (pdf)
"Intermolecular [3+3]-Cycloadditions of Azides with the Nazarov Intermediate," Owen Scadeng, Michael J. Ferguson, F. G. West, Org. Lett. 2011, 13, 114-117. (pdf)
"Olefination of α,α′-Divinyl Ketones through Catalytic Meyer−Schuster Rearrangement," Curtis J. Rieder, Karl J. Winberg, F. G. West, J. Org. Chem. 2011, 76, 50-56. (pdf)
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