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Stereoselective synthesis of a C1–C6 fragment of pinnatoxin A via a 1,4-addition/alkylation sequence

Authors
Publisher
Elsevier Ltd
Publication Date
Volume
19
Issue
9
Identifiers
DOI: 10.1016/j.tetasy.2008.04.013

Abstract

Abstract A C1–C6 fragment of pinnatoxin A, (5 S,6 R)-5,6-dimethyl-3-methyleneoxepan-2-one, which features a γ,δ- trans-dimethyl-substituted α-methylene lactone, has been synthesized in an enantiomerically pure form from ethyl ( E)-4-benzyloxy-2-butenoate through an auxiliary-based conjugate addition and alkylation reaction. The excellent diastereoselectivity (98:2) observed in the alkylation reaction is the result of stereocontrol from both the adjacent stereocenter and the chiral oxazolidinone.

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