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Diastereoselctive Synthesis of Enantiopure γ–Butenolide-butyrolactones towards Pseudopterogorgia Lactone Furanocembranoid Substructures

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Lehmann,  Christian W.
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Macabeo, A. P. G., Lehmann, C. W., & Reiser, O. (2012). Diastereoselctive Synthesis of Enantiopure γ–Butenolide-butyrolactones towards Pseudopterogorgia Lactone Furanocembranoid Substructures. Synlett, 23(20), 2909-2912. doi:10.1055/s-0032-1317555.


Cite as: http://hdl.handle.net/11858/00-001M-0000-000E-EBBE-E
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.