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Paper | Regular issue | Vol 71, No. 3, 2007, pp.557-567
Published online, 23rd January, 2007
DOI: 10.3987/COM-06-10955
Wittig-Horner-Emmons Reactions of Triethyl 3-Methylphosphonocrotonate with 3-Formylchromones En Route to Benzophenone-Based Retinoid Candidates

Weilin Sun, Shyam Desai, Huri Piao, Patrick Carroll, and Daniel J. Canney*

*Department of Pharmaceutical Sciences, School of Pharmacy, Temple University, 3307 N. Broad Street, Philadelphia, PA 19140, USA


Wittig-Horner-Emmons (WHE) reaction conditions were used in conjunction with other reactions to prepare benzophenone-based retinoid candidates. The chromone nucleus was reacted with triethyl 3-methyl-phosphonocrotonate to afford benzophenones following a known rearrangement of a reaction intermediate. Confirmations of the structure of rearranged products are provided in the form of the X-ray crystal structures and speculation regarding the mechanism for the rearrangements is included. The method provides a facile route to substituted benzophenone-based candidate ligands for retinoic acid receptors (RARs) or for a wide variety of other applications.