Total Synthesis of the Antitumor Antibiotic Basidalin
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- 作者：Jaime A. M. Acosta ; Ramesh Muddala ; Luiz C. A. Barbosa ; John Boukouvalas
- 刊名：Journal of Organic Chemistry
- 出版年：2016
- 出版时间：August 5, 2016
- 年：2016
- 卷：81
- 期：15
- 页码：6883-6886
- 全文大小：291K
- 年卷期：0
- ISSN：1520-6904
文摘
The first synthesis of the tetronamide antibiotic basidalin was accomplished in five steps and 39% overall yield from readily available 4-bromo-2-triisopropylsilyloxyfuran and 2-formyl-1,3-dithiane. Highlights include: (i) regio- and stereocontrolled assemblage of a pivotal (Z)-γ-ylidene-β-bromobutenolide intermediate by stereodirected vinylogous aldol condensation (SVAC), (ii) installation of the amino group via aza-Michael addition/elimination, and crucially (iii) facile access to basidalin by late-stage dithiane removal.