Direct Entry to 4,10-Didesmethyl (9S)-Dihydroerythronolide A via Catalytic Allene Osmylation

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• 作者：Libing Yu ; Huan Wang ; Novruz G. Akhmedov ; Christopher Sowa ; Kai Liu ; Hiyun Kim ; Lawrence Williams
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：June 17, 2016
• 年：2016
• 卷：18
• 期：12
• 页码：2868-2871
• 全文大小：386K
• 年卷期：0
• ISSN：1523-7052

文摘

Desmethyl erythronolides have emerged as macrolide targets that may prove effective against resistant bacteria. A five-step sequence to 4,10-didesmethyl (9S)-dihydroerythronolide A (1) from known cyclic bis[allene] 13 is reported. Key structural and mechanistic aspects of the synthesis are discussed along with catalytic allene osmylation. An improved route to 13 is also described.