Abstract
AbstractThe first total synthesis of the cytotoxic oxylipin Topsentolide B3 has been accomplished in 15 steps with an overall yield of 24 %. Starting with readily available cis‐butene diol as a synthon, the synthesis involved Marouka allylation and Sharpless hydroxylation for the construction of three asymmetric centers. The nine‐membered lactone ring was built through a selective Grubbs ring‐closing metathesis reaction. Other key steps in the synthesis are CuI‐mediated alkynylation and Swern oxidation reactions. This provides a unique approach to the synthesis of oxylipins and offers the advantages of brevity and relatively high overall yield.
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