Highly efficient synthesis of medium-sized lactams via intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester: Synthesis and biological evaluation of LY411575 analogues

Haruhiko Fuwa, Yumiko Okamura, Yuichi Morohashi, Taisuke Tomita, Takeshi Iwatsubo, Toshiyuki Kan, Tohru Fukuyama, Hideaki Natsugari

Research output: Contribution to journalArticlepeer-review

48 Citations (Scopus)

Abstract

A highly efficient method for the synthesis of medium-sized lactams based on intramolecular Staudinger-aza-Wittig reaction of ω-azido pentafluorophenyl ester has been developed. A variety of 7-10 membered lactams were synthesized in excellent yields. Application of the method to the synthesis of analogues of a potent γ-secretase inhibitor LY411575 and their biological evaluation are also described.

Original languageEnglish
Pages (from-to)2323-2326
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number11
DOIs
Publication statusPublished - 2004 Feb 8
Externally publishedYes

Keywords

  • Aza-Wittig reaction
  • Medium-sized lactams
  • Staudinger reaction
  • Structure-activity relationship
  • γ-Secretase inhibitor

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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