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Synlett 2009(14): 2333-2337  
DOI: 10.1055/s-0029-1217725
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Highly Functionalized Spirocyclohexadienones from Morita-Baylis-Hillman Adducts

Rodrigo V. Pirovani, Bruno R. V. Ferreira, Fernando Coelho*
Laboratory of Synthesis of Natural Products and Drugs, University of Campinas, DQO/IQ, PO Box 6154, 13084-971, Campinas, SP, Brazil
Fax: +55(19)37883023; e-Mail: coelho@iqm.unicamp.br;
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Publication History

Received 14 April 2009
Publication Date:
31 July 2009 (online)

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Abstract

Spirohexadienone is a structural moiety present in several biologically active natural products isolated both from terrestrial and marine natural sources. This structural moiety is commonly and strictly related to the biological properties exhibited by the natural products. We show herein that the combination of intermolecular Heck reactions with a phenolic oxidation induced by hypervalent iodine form these structural moieties from Morita-Baylis-Hillman adducts in moderate to good overall yields.

Key words

Morita-Baylis-Hillman - Heck reaction - spiro compounds - palladacycles - hypervalent iodine

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