Efficient approach to the oppolzer-kametani intermediate for estrone methyl ether using the conjugate addition-enolate methylation of the cyclopentenone containing an α-appended benzocyclobutane moiety

Takashi Takahashi, Katsuya Shimizu, Takayuki Doi, Jiro Tsuji, Keiji Yamamoto

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Simple synthesis of (±)-estrone methyl ether by the conjugate addition-enolate methylation of the 2-alkylcyclopentenone followed by the intramolecular Diels-Alder reaction of the o-quinodimethane, and discussions for the diastereoselectivity in the enolatemethylation based on the MM2 transition structure model are presented.

Original languageEnglish
Pages (from-to)4999-5002
Number of pages4
JournalTetrahedron Letters
Volume30
Issue number37
DOIs
Publication statusPublished - 1989
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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