Synthesis of indenol- and azulenol derivatives via platinum dichloride-catalyzed intramolecular hydroxy- or alkoxycyclization of cyclic dienynes

Ming Chang P. Yeh, Wen Cheng Tsao, Sau Tin Cheng

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

(Chemical Equation Presented) Platinum dichloride-catalyzed hydroxy- or alkoxycyclization of cyclohexadienynes gives indenol derivatives, whereas hydroxy- or alkoxycyclization of cycloheptadienynes produces azulenol derivatives. The cyclization reaction proceeds via a cyclopropyl platinacarbene intermediate and allows for the direct stereocontrol of three contiguous stereogenic centers of the fused bicyclic skeletons. The transient reactive intermediate obtained from PtCl 2 -catalyzed cyclization reaction of a cyclohexadienyndiol can be trapped intramolecularly by a hydroxyl group to afford an oxatricyclo[5.4.0.0 4,8 ]-undecane ring skeleton with extreme diastereoselectivity.

Original languageEnglish
Pages (from-to)2902-2904
Number of pages3
JournalJournal of Organic Chemistry
Volume73
Issue number7
DOIs
Publication statusPublished - 2008 Apr 4

ASJC Scopus subject areas

  • Organic Chemistry

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