Building trans-bicyclo[4.4.0]decanes/decenes in complex multifunctional frameworks: the case for antibiotic development

Wanli Zhang; Anna R. Kaplan; Emma K. Davison; Jared L. Freeman; Margaret A. Brimble; William M. Wuest

doi:10.1039/D0NP00052C

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Building trans-bicyclo[4.4.0]decanes/decenes in complex multifunctional frameworks: the case for antibiotic development

Wanli Zhang,†^a Anna R. Kaplan,†^a Emma K. Davison,

^bcd Jared L. Freeman,

^bd Margaret A. Brimble

^bcd and William M. Wuest

*^ae

Author affiliations

* Corresponding authors

^a Department of Chemistry, Emory University, USA
E-mail: wwuest@emory.edu

^b School of Chemical Sciences, University of Auckland, 23 Symonds St., Auckland, New Zealand

^c School of Biological Sciences, University of Auckland, 23 Symonds St., Auckland, New Zealand

^d The Maurice Wilkins Centre for Molecular Biodiscovery, University of Auckland, Private Bag 92019, Auckland, New Zealand

^e Emory Antibiotic Resistance Center, Emory School of Medicine, USA

Abstract

Covering: 2000 to 2020.

trans-Bicyclo[4.4.0]decane/decene (such as trans-decalin and trans-octalin)-containing natural products display a wide range of structural diversity and frequently exhibit potent and selective antibacterial activities. With one of the major factors in combatting antibiotic resistance being the discovery of novel scaffolds, the efficient construction of these natural products is an attractive pursuit in the development of novel antibiotics. This highlight aims to provide a critical analysis on how the presence of dense architectural and stereochemical complexity necessitated special strategies in the synthetic pursuits of these natural trans-bicyclo[4.4.0]decane/decene antibiotics.

Graphical abstract: Building trans-bicyclo[4.4.0]decanes/decenes in complex multifunctional frameworks: the case for antibiotic development

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Article information

DOI: https://doi.org/10.1039/D0NP00052C
Article type: Highlight
Submitted: 20 Jul 2020
First published: 18 Nov 2020

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Nat. Prod. Rep., 2021,38, 880-889

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Building trans-bicyclo[4.4.0]decanes/decenes in complex multifunctional frameworks: the case for antibiotic development

W. Zhang, A. R. Kaplan, E. K. Davison, J. L. Freeman, M. A. Brimble and W. M. Wuest, Nat. Prod. Rep., 2021, 38, 880 DOI: 10.1039/D0NP00052C

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Building trans-bicyclo[4.4.0]decanes/decenes in complex multifunctional frameworks: the case for antibiotic development

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Building trans-bicyclo[4.4.0]decanes/decenes in complex multifunctional frameworks: the case for antibiotic development

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