Abstract
To unambiguously establish the stereostructure of the marine cytotoxic bromotriterpenoid iubol, a member of the thyrsiferol family, asymmetric chemical synthesis has been carried out. The synthesis features a one-pot process for the tetrahydropyranyl D ring construction through a stoichiometric Sharpless asymmetric epoxidation of allylic alcohols followed by titanium chelation-assisted 6-exo oxacyclization. In this paper, we report the asymmetric total synthesis of iubol, revision of the proposed structure to the C22-epimer, and preliminary cytotoxic activities of synthetic compounds against some tumor cells.
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