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

• Nakamura, Seiichi

• Kikuchi, Fumiaki

• Hashimoto, Shunichi

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.

Journal

• Tetrahedron Asymmetry

  Tetrahedron Asymmetry 19 (9), 1059-1067, 2008-05-16

  Pergamon

Details

• CRID: 1050564288948762240
• NII Article ID: 120000952006
• NII Book ID: AA1074621X
• HANDLE: 2115/33049
• ISSN: 09574166
• Text Lang: en
• Article Type: journal article
• Data Source:
  • IRDB
  • CiNii Articles
  • KAKEN