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Synlett 2003(14): 2234-2236  
DOI: 10.1055/s-2003-42059
LETTER
© Georg Thieme Verlag Stuttgart · New York

An Expeditious Synthesis of (±)-Mimosifoliol Utilizing a Cascade Involving an o-Quinone Methide Intermediate

Kristin Tuttle, Andrew A. Rodriguez, Thomas R. R. Pettus*
Department of Chemistry and Biochemistry, University of California at Santa Barbara, Santa Barbara, CA 93106-9510, USA
Fax: +1(805)8935690; e-Mail: Pettus@chem.ucsb.edu;
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Publication History

Received 25 May 2003
Publication Date:
07 October 2003 (online)

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Abstract

An efficient synthesis of (±)-mimosifoliol is reported. The key transformation involves a domino sequence leading to an o-quinone methide and its subsequent consumption in 1,4-conjugate addition with a vinyl Grignard reagent.

Key words

alcohols - aldehydes - domino reactions - natural products - Michael additions - Grignard reactions - enones - eliminations - protecting groups - quinones - regioselectivity - tandem reactions - ­total synthesis