Highly stereoselective synthesis of mupirocin H

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• 作者：Sandip Sengupta^a ; Hak Joong Kim^b ; Kyung Seon Cho^a ; Woon Young Song^b ; Taebo Sim^a ; ^c ; ^{tbsim@kist.re.kr}
• 关键词：Mupirocin H ; Total synthesis ; (+)-(R)-Roche ester ; Grubbs cross metathesis
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：23 February 2017
• 年：2017
• 卷：73
• 期：8
• 页码：1182-1189
• 全文大小：725 K
• 卷排序：73

文摘

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.