The total synthesis of swinholide A. Part 1: A stereocontrolled synthesis of a C19-C32 segment

Add time:09/03/2019    Source:sciencedirect.com

The C19-C32 segment 10 of swinholide A was prepared in 15 steps (8% yield, 82% ds) from (±)-16. Key steps include (i) the Sharpless epoxidation, 16 → 17, (ii) the acetal allylation, 15 → 23, (iii) the anti aldol addition, 13 + 14 → 12, and (iv) the alkene hydroboration, 30 → 31. The swinholides are a series of complex polyketide macrodiolides, which display potent cytotoxicity against a variety of human tumour cell lines. 1,2 Swinholide A, isolated from the marine sponge Theonella swinhoei, was first reported as an antifungal agent by Carmely and Kashman in 1985.1 Using NMR methods and chemical

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