Literature DB >> 23088749

A chiron approach to the total synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin.

Rodney A Fernandes1, Vijay P Chavan, Sandip V Mulay, Amarender Manchoju.   

Abstract

A general, efficient, and common strategy for the synthesis of (-)-juglomycin A, (+)-kalafungin, (+)-frenolicin B, and (+)-deoxyfrenolicin is reported here. The strategy involves the synthesis of a key building block alkyne from a cheap chiral pool material, D-glucono-δ-lactone, Dötz benzannulation, oxa-Pictet-Spengler reaction, and H(2)SO(4)-mediated epimerization.

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Year:  2012        PMID： 23088749     DOI： 10.1021/jo3019939

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  5 in total

1.  Ruthenium(0) Catalyzed Endiyne-α-Ketol [4 + 2] Cycloaddition: Convergent Assembly of Type II Polyketide Substructures via C-C Bond Forming Transfer Hydrogenation.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  J Am Chem Soc       Date:  2015-05-04       Impact factor: 15.419

2.  A diastereoselective oxa-Pictet-Spengler-based strategy for (+)-frenolicin B and epi-(+)-frenolicin B synthesis.

Authors:  Yinan Zhang; Xiachang Wang; Manjula Sunkara; Qing Ye; Larissa V Ponomereva; Qing-Bai She; Andrew J Morris; Jon S Thorson
Journal:  Org Lett       Date:  2013-10-23       Impact factor: 6.005

3.  Ruthenium(0)-Catalyzed [4+2] Cycloaddition of Acetylenic Aldehydes with α-Ketols: Convergent Construction of Angucycline Ring Systems.

Authors:  Aakarsh Saxena; Felix Perez; Michael J Krische
Journal:  Angew Chem Int Ed Engl       Date:  2015-12-09       Impact factor: 15.336

4.  Frenolicins C-G, pyranonaphthoquinones from Streptomyces sp. RM-4-15.

Authors:  Xiachang Wang; Khaled A Shaaban; Sherif I Elshahawi; Larissa V Ponomareva; Manjula Sunkara; Yinan Zhang; Gregory C Copley; James C Hower; Andrew J Morris; Madan K Kharel; Jon S Thorson
Journal:  J Nat Prod       Date:  2013-08-14       Impact factor: 4.050

5.  Total Synthesis of 6-Deoxydihydrokalafungin, a Key Biosynthetic Precursor of Actinorhodin, and Its Epimer.

Authors:  Takuya Kumamoto; Mika Kainuma; Azusa Takahashi; Yoshika Matsuo; Kazuaki Katakawa; Takaaki Taguchi; Koji Ichinose
Journal:  Molecules       Date:  2021-10-22       Impact factor: 4.411
  5 in total

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