A new synthesis of α-methylene lactones

Toru Minami, Kazunari Hirakawa, Shinichiro Koyanagi, Seigo Nakamura, Masahiko Yamaguchi

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

Various α-diethoxyphosphoryl-γ, δ-unsaturated acids were synthesized in good yields via alkylation of ethyl (diethoxyphosphoryl)acetate with allylic bromides. Iodo- and seleno-lactonization led to α-phosphono-iodo and -seleno lactones, which underwent Wittig-Horner reaction with paraformaldehyde to produce α-methylene-γ-lactones in very good yields. This methodology was applied to a short synthesis of frullanolide.

Original languageEnglish
Pages (from-to)2385-2390
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number9
DOIs
Publication statusPublished - 1990

ASJC Scopus subject areas

  • Chemistry(all)

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