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Communication | Special issue | Vol 59, No. 2, 2003, pp.491-495
Published online, 1st January, 1970
DOI: 10.3987/COM-02-S72
A New Route to the Calcitriol A-Ring Precursor Using a Bicyclo[3.2.1]octane Chiral Building Block

Norio Miyazawa, Ayako Tosaka, Keisuke Hanada, and Kunio Ogasawara*

*Pharnaceutical Institute, Tohoku University, Aramaki, Aoba-ku, sendai 980-8578, Japan

Abstract

A concise route to the A-ring precursor of calcitriol (1α,25-dihydroxyvitamin D3) has been developed starting from the chiral building block having a bicyclo[3.2.1]octane framework. Since we have already developed a diastereocontrolled synthesis of the C/D-ring precursor starting with the enantiomeric chiral building block, the present synthesis implies the total synthesis of calcitriol from a single precursor in a formal sense.