Total Synthesis of (−)-Mucosin and Revision of Structure

The first total synthesis of (−)-mucosin
(6), an unusual marine hydrindane natural product incorporating
a prostaglandin-like
submotif, has been achieved. As a result of the campaign, three of
the four all-carbon stereocenters in the purported structure 1 have been revised. Of particular note is the excellent control
over β-chirality in conjugate addition to ester (−)-22 and the facial selectivity in the subsequent protonation
of an intermediate silyl ketene acetal.