Highly stereoselective synthesis of mupirocin H

Title
Highly stereoselective synthesis of mupirocin H
Authors
심태보Sandip SenguptaHak Joong KimKyung Seon ChoWoon Young Song
Issue Date
2017-02
Publisher
Tetrahedron
Citation
VOL 73, NO 8-1189
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.
URI
http://pubs.kist.re.kr/handle/201004/69794
ISSN
0040-4020
Appears in Collections:
KIST Publication > Article
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