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Review | Special issue | Vol 79, No. 1, 2009, pp.145-162
Published online, 28th November, 2008
DOI: 10.3987/REV-08-SR(D)3
Synthesis of 1α,25-Dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (Eldecalcitol) and Related Compounds by the Trost Convergent Methodology

Noboru Kubodera* and Susumi Hatakeyama

*Chugai Pharmaceutical Company, Ltd., 2-1-1, Nihonbashi-Muromachi, Chuo-ku, Tokyo 103-8324, Japan

Abstract

Using Trost convergent methodology, the synthesis of 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (eldecalcitol) for the improved and industrial scale production and related putative metabolites of eldecalcitol is summarized. In addition, A-ring diastereomers at the 1- and 3-positions of eldecalcitol are described. The synthesis centers on a key palladium-catalyzed alkylative cyclization and coupling of ene-ynes that constitute the A-ring fragment to bromomethylenes comprising the C/D-ring fragment which affords the requisite triene framework of vitamin D3 analogs.