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Paper | Special issue | Vol 90, No. 1, 2015, pp.442-461
Published online, 4th August, 2014
DOI: 10.3987/COM-14-S(K)42
Total Synthesis of Marine Sesquiterpenoid Sinularianin B and 8-epi-Sinularianin B

Koichiro Ota and Hiroaki Miyaoka*

*School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan

Abstract

The enantioselective total synthesis of marine sesquiterpenoid sinularianin B, isolated from the Formosan soft coral Sinularia sp., has been accomplished in 16 steps based on a highly concise synthetic strategy. The synthesis features two highly stereoselective sulfone-mediated reactions, including a key tandem intermolecular−intramolecular alkylation developed in our laboratory, and a palladium-catalyzed desulfonylation of an allyl sulfone through π-allyl palladium complex formation.