Development of diastereoselective birch reduction-alkylation reactions of bi- and tricyclic β-alkoxy-α,β-unsaturated ketones

Kou Hiroya, Yusuke Ichihashi, Ai Furutono, Kiyofumi Inamoto, Takao Sakamoto, Takayuki Doi

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

(Chemical Equation Presented) Diastereoselective Birch reduction-alkylation reactions of bicyclic β-alkoxy-α,β-unsaturated carbonyl compounds and tricyclic analogues were investigated. Although the relative configuration of the product was altered according to the structure of the starting material, stereoselectivity of the reaction could be accounted for by similar reaction pathways. The product from the tricyclic β-alkoxy-α, β-unsaturated carbonyl compound corresponded to the trichothecene skeleton.

Original languageEnglish
Pages (from-to)6623-6630
Number of pages8
JournalJournal of Organic Chemistry
Volume74
Issue number17
DOIs
Publication statusPublished - 2009 Sep 4

ASJC Scopus subject areas

  • Organic Chemistry

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