Literature DB >> 33206093

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

Wanli Zhang1, Anna R Kaplan1, Emma K Davison2, Jared L Freeman3, Margaret A Brimble2, William M Wuest4.   

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.

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Year:  2021        PMID: 33206093      PMCID: PMC8322967          DOI: 10.1039/d0np00052c

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN: 0265-0568            Impact factor:   13.423


  44 in total

1.  UCS1025A, a novel antibiotic produced by Acremonium sp.

Authors:  R Nakai; H Ogawa; A Asai; K Ando; T Agatsuma; S Matsumiya; S Akinaga; Y Yamashita; T Mizukami
Journal:  J Antibiot (Tokyo)       Date:  2000-03       Impact factor: 2.649

2.  Asymmetric Total Synthesis of the Naturally Occurring Antibiotic Anthracimycin.

Authors:  Emma K Davison; Jared L Freeman; Wanli Zhang; William M Wuest; Daniel P Furkert; Margaret A Brimble
Journal:  Org Lett       Date:  2020-06-29       Impact factor: 6.005

3.  Synthesis of the C7-C15 trans decalin portion of the natural antibiotic tetrodecamycin.

Authors:  Jeffrey M Warrington; Louis Barriault
Journal:  Org Lett       Date:  2005-10-13       Impact factor: 6.005

4.  Total synthesis of UCS1025A.

Authors:  Tristan H Lambert; Samuel J Danishefsky
Journal:  J Am Chem Soc       Date:  2006-01-18       Impact factor: 15.419

5.  Enantioselective organocatalytic intramolecular Diels-Alder reactions. The asymmetric synthesis of solanapyrone D.

Authors:  Rebecca M Wilson; Wendy S Jen; David W C Macmillan
Journal:  J Am Chem Soc       Date:  2005-08-24       Impact factor: 15.419

6.  Anthracimycin, a potent anthrax antibiotic from a marine-derived actinomycete.

Authors:  Kyoung Hwa Jang; Sang-Jip Nam; Jeffrey B Locke; Christopher A Kauffman; Deanna S Beatty; Lauren A Paul; William Fenical
Journal:  Angew Chem Int Ed Engl       Date:  2013-06-17       Impact factor: 15.336

7.  Fermentation, isolation and characterization of antibiotic PR-1350.

Authors:  N R Andersen; H O Lorck; P R Rasmussen
Journal:  J Antibiot (Tokyo)       Date:  1983-07       Impact factor: 2.649

8.  Two of a Kind--The Biosynthetic Pathways of Chlorotonil and Anthracimycin.

Authors:  Katrin Jungmann; Rolf Jansen; Klaus Gerth; Volker Huch; Daniel Krug; William Fenical; Rolf Müller
Journal:  ACS Chem Biol       Date:  2015-09-08       Impact factor: 5.100

9.  Chlorotonil A, a macrolide with a unique gem-dichloro-1,3-dione functionality from Sorangium cellulosum, So ce1525.

Authors:  Klaus Gerth; Heinrich Steinmetz; Gerhard Höfle; Rolf Jansen
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

Review 10.  Penicillin's Discovery and Antibiotic Resistance: Lessons for the Future?

Authors:  Mariya Lobanovska; Giulia Pilla
Journal:  Yale J Biol Med       Date:  2017-03-29
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  2 in total

1.  Structural Analysis of the Michael-Michael Ring Closure (MIMIRC) Reaction Products.

Authors:  Mabel M Montenegro-Sustaita; Hugo A Jiménez-Vázquez; Elena Vargas-Díaz; J Enrique Herbert-Pucheta; L Gerardo Zepeda-Vallejo
Journal:  Molecules       Date:  2022-04-28       Impact factor: 4.927

Review 2.  Natural Products in Cancer Therapy: Past, Present and Future.

Authors:  Min Huang; Jin-Jian Lu; Jian Ding
Journal:  Nat Prod Bioprospect       Date:  2021-01-03
  2 in total

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