Total Synthesis of Clavosolide†A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction.

ABSTRACT

The 20-membered marine macrodiolide clavosolide A is prepared in 7 steps (LLS) in the absence of protecting groups or chiral auxiliaries via enantioselective alcohol-mediated carbonyl addition. In 9 prior total syntheses, 11-34 steps (LLS) were required.