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Total Synthesis of (−)-Teucvidin

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posted on 01.06.2012, 00:00 by Xiaozu Liu, Chi-Sing Lee
A concise enantioselective synthesis of (−)-teucvidin has been achieved. Our synthetic strategy involved the diastereoselective Michael/Conia–ene cascade cyclization reaction for rapid establishment of the cis-decalin skeleton with three new stereogenic centers in one pot (72%, single diastereomer), the epoxidation/dealkoxycarbonylation protocol for construction of the fused furanone moiety, and the O-allylation/Claisen rearrangement protocol for construction of the all-carbon quaternary center at C9 of the clerodane skeleton.