An Efficient Formal Synthesis of (-)-Clavosolide A Featuring a Mismatched Stereoselective Oxocarbenium Reduction

The enantioselective formal synthesis of the polyketide marine natural Product (-)-clavosolide A is presented. The construction of the beta-C-glycoside subunit is highlighted by a one-pot oxocarbenium cation formation/reduction sequence. Yamaguchi dimerization afforded the diolide aglycon in 18 steps (longest linear sequence).