Tetrahedron Asymmetry p. 1059 - 1067 (2008)
Update date:2022-07-30
Topics:
Nakamura, Seiichi
Kikuchi, Fumiaki
Hashimoto, Shunichi
A C1-C6 fragment of pinnatoxin A, (5S,6R)-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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