Total Synthesis of Applanatumol B
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Published on: October 27, 2011
Kyohei Uchida1, Yuichiro Kawamoto1, Toyoharu Kobayashi1
1School of Life Sciences , Tokyo University of Pharmacy and Life Sciences , Hachioji , Tokyo 192-0392 , Japan.
Abstract:
The first total synthesis of the tricyclic meroterpenoid applanatumol B, isolated from Ganoderma applanatum, was accomplished in 14 steps from 2,5-dimethoxybenzaldehyde and 4-pentyn-1-ol. The synthetic features include an intramolecular Morita-Baylis-Hillman reaction, a stereoselective Michael addition, and efficient construction of the tricyclic skeleton under acidic conditions involving epimerization at the α-position of the ketone.
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