Synthesis of the phenanthrene and cyclohepta[ a ]naphthalene skeletons via gold(I)-catalyzed intramolecular cyclization of unactivated cyclic 5-(2-arylethyl)-1,3-dienes

Ming Chang P. Yeh, Ming Nan Lin, Yi Shiang Chou, Tern Chi Lin, Li Yu Tseng

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

The gold(I)-catalyzed hydroarylation of cyclohexa-1,3-dienes bearing an aryl group and a gem-diester in the tether proceeds in a 1,4-addition manner and in a diastereoselective fashion to afford perhydrophenanthrene rings. The reaction proceeded via attack of the aryl group onto the gold-activated cyclic dienes followed by rearomatization and protodeauration to generate perhydrophenanthrenes in good yields. This hydroarylation can be applied to the synthesis of perhydrocyclohepta[a]naphthalenes from aryl-tethered cycloheptadienes and the gold(I) catalyst.

Original languageEnglish
Pages (from-to)4027-4033
Number of pages7
JournalJournal of Organic Chemistry
Volume76
Issue number10
DOIs
Publication statusPublished - 2011 May 20

ASJC Scopus subject areas

  • Organic Chemistry

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