First stereoselective total synthesis and reconfirmation of absolute structure of nonenolide (−)-stagonolide D

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• 作者：A. Sravanth Kumar^a ; ^b ; ¹ ; K. Praneeth^b ; ¹ ; P. Srihari^b ; ^{srihari@iict.res.in} ; J.S. Yadav^a ; ^b ; ^{yadavpub@gmail.com}
• 关键词：Macrolides ; Yamaguchi esterification ; Epoxidation ; Stereoselective reduction ; Phytotoxic
• 刊名：Tetrahedron Letters
• 出版年：2017
• 出版时间：8 February 2017
• 年：2017
• 卷：58
• 期：6
• 页码：509-511
• 全文大小：445 K
• 卷排序：58

文摘

The first total synthesis of an unique compound stagonolide D is achieved. The strategy followed is a convergent approach and amenable for large scale reaction. Midland Alpine borane reduction and Henbest epoxidation reactions are key reactions. The total synthesis was achieved in 8 shortest steps starting from R-glycidol. By maneuvering the reagents, the other isomers can be easily synthesized.