A Concise Synthesis of Mupirocin H Using a Cross‐Metathesis‐Based Strategy. Issue 23 (11th July 2014)

• Record Type: Journal Article
• Authors: Sengupta, Sandip; Sim, Taebo
• Is Part Of: European journal of organic chemistry. Issue 23(2014)
• Page Start: 5063
• Page End: 5070
• Publication Date: 2014-07-11
• Subjects: Total synthesis -- Natural products -- Polyketides -- Metathesis -- Reformatsky reaction; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201402442
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : A highly efficient (10.1 % overall yield) and convergent (longest linear sequence of 16 steps) synthesis of mupirocin H is described, starting from commercially available (+)‐( R )‐Roche ester.