Total Synthesis of Squamotacin

The first total synthesis of (+)-squamotacin, 1, which has shown cytotoxic selectivity for the human prostate tumor cell line, was achieved in 27 steps and 0.83% yield starting with (+)-muricatacin, 4 . All asymmetric centers in the bistetrahydrofuran fragment of the molecules were produced by the Sharpless asymmetric dihydroxylation (AD) and the asymmetric epoxidation (AE) reactions.