Highly stereoselective synthesis of mupirocin H. Issue 8 (23rd February 2017)

• Record Type: Journal Article
• Authors: Sengupta, Sandip; Kim, Hak Joong; Cho, Kyung Seon; Song, Woon Young; Sim, Taebo
• Is Part Of: Tetrahedron. Volume 73:Issue 8(2017)
• Page Start: 1182
• Page End: 1189
• Publication Date: 2017-02-23
• Subjects: Mupirocin H -- Total synthesis -- (+)-(R)-Roche ester -- Grubbs cross metathesis; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2017.01.017
• Languages: English
• ISSNs: 0040-4020

Abstract

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. Graphical abstract: