Abstract
The first total synthesis of the marine-derived cytotoxin topsentolide A2, which eventually culminated in its stereochemical determination, was accomplished in 17 steps from a known chiral alcohol. An improved synthesis of its congener, topsentolide C2, from a synthetic intermediate of topsentolide A2 was also performed by utilizing the Yamaguchi lactonization to construct its nine-membered lactone ring. Treatment of epoxide ring-containing topsentolide A2 with HCl/MeOH brought about its quantitative conversion into topsentolide C2.
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