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

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Title: Stereoselective synthesis of a C1-C6 fragment of pinnatoxin A via a 1,4-addition/alkylation sequence
Authors: Nakamura, Seiichi1 Browse this author
Kikuchi, Fumiaki2 Browse this author
Hashimoto, Shunichi3 Browse this author →KAKEN DB
Authors(alt): 中村, 精一1
菊地, 史朗2
橋本, 俊一3
Issue Date: 16-May-2008
Publisher: Pergamon
Journal Title: Tetrahedron Asymmetry
Volume: 19
Issue: 9
Start Page: 1059
End Page: 1067
Publisher DOI: 10.1016/j.tetasy.2008.04.013
Abstract: A C1–C6 fragment of pinnatoxin A, (5S,6R)-5,6-dimethyl-3-methyleneoxepan-2-one, which features a γ,δ-trans-dimethylsubstituted α-methylene lactone, has been synthesized in an optically 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 would be a result of stereocontrol from both the adjacent stereocenter and the chiral oxazolidinone.
Relation: http://www.sciencedirect.com/science/journal/09574166
Type: article (author version)
URI: http://hdl.handle.net/2115/33049
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 中村 精一

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