Facile synthesis of carbotetracycles via gold(i)-catalyzed cyclization of unactivated cyclic 1-aryl-6,8-dien-1-ynes

Ming Chang P. Yeh, Wen Cheng Tsao, Bo Jen Lee, Tzu G. Lin

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21 Citations (Scopus)

Abstract

The gold(I)-catalyzed cyclization of the cyclohexa-1,3-diene bearing a terminal alkyne and a gemdiester in the tether proceeds via a cationic gold intermediate to give a tetrahydromethyleneindene derivative. Changing the gem-diester to a gem-diketone in the tether, the transient gold-stabilized carbocation is trapped intramolecularly by a methyl ketone to afford a tricyclo[5.4.04,8]undecane ring skeleton. Under the same reaction conditions, aryl-substituted cyclohexadienynes afford hexahydroacephenanthrylene rings in a diastereoselective fashion and in good yields. The reaction proceeded via attack of the aryl group onto the gold-stabilized carbocations followed by aromatization and protodemetalation to generate the tetracarbocycles. This cycloaddition can be applied to the synthesis of pentahydronapthoazulenes from aryl-substituted cycloheptadienynes and the gold(I) catalyst.

Original languageEnglish
Pages (from-to)5326-5332
Number of pages7
JournalOrganometallics
Volume27
Issue number20
DOIs
Publication statusPublished - 2008 Oct 27

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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