Enantiospecific Syntheses of (+)-Crotepoxide, (+)-Boesenoxide, (+)-β-Senepoxide, (+)-Pipoxide Acetate, (-)-iso-Crotepoxide, (-)-Senepoxide, and (-)-Tingtanoxide from (-)-Quinic Acid

Tony K.M. Shing, Eric K.W. Tam

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

A convenient strategy that is ideally suited for the construction of all the naturally occurring cyclohexane diepoxides and cyclohexene epoxides is described. The key intermediate 12, a 1,3-cyclohexadiene, has been prepared from (-)-quinic acid in 11 steps with 18% overall yield. Singlet oxygen photooxygenation of the 1,3-cyclohexadiene followed by rearrangement of the resultant endoperoxides with either cobalt-meso-tetraphenylporphyrin or trimethyl phosphite afforded enantiopure (+)-crotepoxide, (+)-boesenoxide, and (-)-iso-crotepoxide or (-)-senepoxide, (+)-β-senepoxide, (+)-pipoxide acetate, and (-)-tingtanoxide, respectively.

Original languageEnglish
Pages (from-to)1547-1554
Number of pages8
JournalJournal of Organic Chemistry
Volume63
Issue number5
Publication statusPublished - 1998 Mar 6

ASJC Scopus subject areas

  • Organic Chemistry

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