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Synfacts 2010(8): 0852-0852  
DOI: 10.1055/s-0030-1257748
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Tamoxifen Homologue

Contributor(s): Philip Kocienski
K. Endo*, M. Hirokami, T. Shibata*
Waseda University, Tokyo, Japan
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

The tamoxifen homologue G displays high antiestrogenic potency in antiproliferative assays against MCF-7 breast cancer cells (M. J. Meegan et al. J. Med. Chem. 2001, 44, 1072). The tetrasubstituted alkenylboronate E used in the synthesis was derived by lithiation of the organodiboronate C with lithium tetramethyl­piperidide (LiTMP) followed by nucleophilic addition of the organolithium intermediate D to propio­phenone.