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Concise Total Synthesis of (-)-Bipolarolide D
Shengling Sun1,2, Qi Wei1,2, Yufei Liu1,2
1College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, Fujian Province, People's Republic of China.
Abstract:
Here we report the first and concise total synthesis of a complex ophiobolin-derived sesterterpene, bipolarolide D, which hinges on two strategic applications of pentafulvene: (1) enantioselective pentafulvene-involved [6+2] cycloaddition; (2) regioselective and diastereoselective pentafulvene-involved Heck cyclization. Late-stage selective allylic addition to the ketone moiety facilitates the successful installation of the side chain. This strategy enabled the accomplishment of its first enantioselective total synthesis through a modular approach. This synthesis will facilitate the investigation of relevant biological activities and provide a synthetic blueprint for utilizing fulvenes as versatile synthons in other complex natural product synthesis.
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