Highly stereoselective synthesis of mupirocin H

Sandip Sengupta, Hak Joong Kim, Kyung Seon Cho, Woon Young Song, Taebo Sim

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A highly diastereoselective and efficient convergent synthesis of mupirocin H starting from (+)-(R)-Roche ester was achieved. Grubbs cross metathesis was employed as the key step in the pathway to generate an important E-olefin intermediate. Other processes utilized in the route include a Pd-catalysed stereoselective substitution reaction of a cis epoxide, Sharpless epoxidation followed by Red-Al promoted epoxide ring opening, and Seebach methylation and a TEMPO/BAIB mediated oxidation-lactonization sequence. Finally, we observed that mupirocin H inhibits SbnE, a synthetase required for staphyloferrin B biosynthesis.

Original languageEnglish
Pages (from-to)1182-1189
Number of pages8
JournalTetrahedron
Volume73
Issue number8
DOIs
Publication statusPublished - 2017 Feb 23

Keywords

  • (+)-(R)-Roche ester
  • Grubbs cross metathesis
  • Mupirocin H
  • Total synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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