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

研究成果: Article

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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.

元の言語English
ページ(範囲)1547-1554
ページ数8
ジャーナルJournal of Organic Chemistry
63
発行部数5
出版物ステータスPublished - 1998 3 6

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ASJC Scopus subject areas

  • Organic Chemistry

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