Literature DB >> 32598151

Asymmetric Total Synthesis of the Naturally Occurring Antibiotic Anthracimycin.

Emma K Davison1,2,3, Jared L Freeman1,3, Wanli Zhang4, William M Wuest4,5, Daniel P Furkert1,3, Margaret A Brimble1,2,3.   

Abstract

The first total synthesis of the potent antibiotic anthracimycin was achieved in 20 steps. The synthesis features an intramolecular Diels-Alder reaction to forge the trans-decalin moiety, and an unprecedented aldol reaction using a complex β-ketoester to provide the tricarbonyl motif. A Stork-Zhao olefination and Grubbs ring closing metathesis delivered the E/Z-diene and forged the macrocycle. The C2 configuration was set with a base-mediated epimerization, providing access to (-)-anthracimycin.

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Year:  2020        PMID： 32598151      PMCID： PMC8283552          DOI： 10.1021/acs.orglett.0c01913

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  14 in total

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4.  Total synthesis of (-)-goniotrionin.

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Journal:  J Org Chem       Date:  2012-04-03       Impact factor: 4.354

5.  A Novel mTOR Inhibitor; Anthracimycin for the Treatment of Human Hepatocellular Carcinoma.

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8.  Total synthesis and structural elucidation of ent-micropyrone and (+)-ascosalipyrone.

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Journal:  Org Biomol Chem       Date:  2012-07-03       Impact factor: 3.876

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

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Review 10.  Methicillin-resistant Staphylococcus aureus (MRSA) and anti-MRSA activities of extracts of some medicinal plants: A brief review.

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2.  Exploration of Diverse Secondary Metabolites From Streptomyces sp. YINM00001, Using Genome Mining and One Strain Many Compounds Approach.

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Review 3.  Building trans-bicyclo[4.4.0]decanes/decenes in complex multifunctional frameworks: the case for antibiotic development.

Authors:  Wanli Zhang; Anna R Kaplan; Emma K Davison; Jared L Freeman; Margaret A Brimble; William M Wuest
Journal:  Nat Prod Rep       Date:  2021-05-26       Impact factor: 13.423
  3 in total

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