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Synfacts 2008(12): 1243-1243  
DOI: 10.1055/s-0028-1087291
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of an Estrogen Receptor-β Agonist

Contributor(s): Philip Kocienski
J. P. Scott*, M. S. Ashwood, K. M. J. Brands, S. E. Brewer, C. J. Cowden, U.-H. Dolling, K. M. Emerson, A. D. Gibb, A. Goodyear, S. F. Oliver, G. W. Stewart, D. J. Wallace
Merck Sharp & Dohme Research Laboratories, Hoddesdon, UK
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Publication History

Publication Date:
20 November 2008 (online)

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Significance

The target molecule was a candidate for hormone replacement therapy aimed at a treatment for the symptoms of menopause with reduced risk of developing breast cancer, deep vein thrombosis, stroke and cardiovascular disease. The short multikilogram synthesis depicted features a phase-transfer-catalyzed conjugate addition (C → E) mediated by the cinchonine-derived catalyst D. The synthesis involves only six isolated intermediates and avoids chromatographic purification.