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Published on: October 4, 2019
Total Synthesis of the Antitumor Antibiotic Basidalin
Jaime A M Acosta1, Ramesh Muddala1, Luiz C A Barbosa2
1Department of Chemistry, Pavillon Alexandre-Vachon, Université Laval , 1045 Avenue de la Médecine, Quebec City, Quebec G1V 0A6, Canada.
Abstract:
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.
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