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Free keywords:
marine furanocembranoids; asymmetric synthesis; vinylogous Mukaiyama addition; lactones; furans
Abstract:
A diastereoselective methodology for preparing trans-γ-lactone-γ-butenolides through vinylogous aldol additions of siloxyfuranes to enantiopure cyclopropylcarbaldehyde followed by a tin-catalyzed retroaldol-lactonization cascade is reported. This synthetic approach is applied to a short synthesis of an exo-trienol furan lactone substructure relevant to bielschowskysin and other related coral diterpenoid natural products.