A concise synthesis of mupirocin H using a cross-metathesis-based strategy

Sandip Sengupta, Taebo Sim

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A highly efficient (10.1% overall yield) and convergent (longest linear sequence of 16 steps) synthesis of mupirocin H has been achieved, starting from commercially available (+)-(R)-Roche ester. The route relies on an efficient Grubbs cross-metathesis reaction to generate a key, late-stage E-olefin intermediate, and a cobalt-catalysed diastereoselective Reformatsky reaction to produce a β-hydroxy ester that serves as a late-stage intermediate.

Original languageEnglish
Pages (from-to)5063-5070
Number of pages8
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number23
DOIs
Publication statusPublished - 2014 Jan 1

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Mupirocin
metathesis
esters
Esters
Alkenes
synthesis
Cobalt
alkenes
cobalt
routes

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

A concise synthesis of mupirocin H using a cross-metathesis-based strategy. / Sengupta, Sandip; Sim, Taebo.

In: European Journal of Organic Chemistry, Vol. 2014, No. 23, 01.01.2014, p. 5063-5070.

Research output: Contribution to journalArticle

Sengupta, Sandip ; Sim, Taebo. / A concise synthesis of mupirocin H using a cross-metathesis-based strategy. In: European Journal of Organic Chemistry. 2014 ; Vol. 2014, No. 23. pp. 5063-5070.
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