Literature DB >> 33828615

Synthesis of legonmycins A and B, C(7a)-hydroxylated bacterial pyrrolizidines.

Wilfred J M Lewis1, David M Shaw2,3, Jeremy Robertson1.   

Abstract

A one-flask, two-step procedure from 3-amino-2-methyl-5,6,7,7a-tetrahydro-1H-pyrrolizin-1-one affords the Streptomyces secondary metabolites legonmycins A and B - three operations overall from methyl N-Boc-prolinate. The key step proceeds in each case via N,O-diacylation, then selective oxidative hydrolysis of the intermediate bicyclic pyrrole and establishes a precedent for the synthesis of related C(7a)-hydroxylated pyrrolizidines.
Copyright © 2021, Lewis et al.

Entities:  

Keywords:  acyloxypyrroles; bacterial pyrrolizidines; cyanoketones; legonmycin; vinylogous ureas

Year:  2021        PMID： 33828615      PMCID： PMC7871033          DOI： 10.3762/bjoc.17.31

Source DB:  PubMed          Journal:  Beilstein J Org Chem        ISSN： 1860-5397            Impact factor:   2.883


  21 in total

1.  Structure reassignment and synthesis of Jenamidines A1/A2, synthesis of (+)-NP25302, and formal synthesis of SB-311009 analogues.

Authors:  Jeremy R Duvall; Fanghui Wu; Barry B Snider
Journal:  J Org Chem       Date:  2006-10-27       Impact factor: 4.354

2.  Metal-Free Regioselective Hypervalent Iodine-Mediated C-2 and C-3 Difunctionalization of N-Substituted Indoles.

Authors:  Dongdong Xu; Wen-Wu Sun; Yanli Xie; Ji-Kai Liu; Bin Liu; Yingbi Zhou; Bin Wu
Journal:  J Org Chem       Date:  2016-11-03       Impact factor: 4.354

3.  Clazamycin B is antibiotic 354.

Authors:  L A Dolak; C DeBoer
Journal:  J Antibiot (Tokyo)       Date:  1980-01       Impact factor: 2.649

4.  Quinohemanine, a quinoxalinone-bohemamine hybrid compound from Streptomyces sp. CPCC 200497.

Authors:  Bingya Jiang; Wei Zhao; Shufen Li; Hongyu Liu; Liyan Yu; Weixiao Niu; Hongwei He; Linzhuan Wu
Journal:  J Antibiot (Tokyo)       Date:  2018-08-29       Impact factor: 2.649

Review 5.  Pyrrolizidine alkaloids: occurrence, biology, and chemical synthesis.

Authors:  Jeremy Robertson; Kiri Stevens
Journal:  Nat Prod Rep       Date:  2017-01-04       Impact factor: 13.423

6.  Synthetic routes to pyrrolizine-1,5-dione derivatives by flash vacuum pyrolysis of amidomethylene derivatives of Meldrum's acid.

Authors:  Hamish McNab; Mark Morrow; Simon Parsons; David A Shannon; Kirsti Withell
Journal:  Org Biomol Chem       Date:  2009-10-01       Impact factor: 3.876

7.  New cell-cell adhesion inhibitors from Streptomyces sp. UMA-044.

Authors:  Qinglin Zhang; Kevin K Schrader; Hala N ElSohly; Satoshi Takamatsu
Journal:  J Antibiot (Tokyo)       Date:  2003-08       Impact factor: 2.649

8.  Jenamidines A to C: unusual alkaloids from Streptomyces sp. with specific antiproliferative properties obtained by chemical screening.

Authors:  Jin-Feng Hu; Dirk Wunderlich; Ralf Thiericke; Hans-Martin Dahse; Susanne Grabley; Xiao-Zhang Feng; Isabel Sattler
Journal:  J Antibiot (Tokyo)       Date:  2003-09       Impact factor: 2.649

9.  Spithioneines A and B, Two New Bohemamine Derivatives Possessing Ergothioneine Moiety from a Marine-Derived Streptomyces spinoverrucosus.

Authors:  Peng Fu; John B MacMillan
Journal:  Org Lett       Date:  2015-05-29       Impact factor: 6.005

10.  1,3-Oxazin-6-one Derivatives and Bohemamine-Type Pyrrolizidine Alkaloids from a Marine-Derived Streptomyces spinoverrucosus.

Authors:  Peng Fu; Scott La; John B MacMillan
Journal:  J Nat Prod       Date:  2015-10-21       Impact factor: 4.050
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