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Asymmetric synthesis of 1α,25-dihydroxyvitamin D3 A-ring precursor starting with 5-tert-butyldimethylsiloxy-2-cyclohexenone

✍ Scribed by Georges P.J Hareau; Masakazu Koiwa; Fumie Sato

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 113 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00169-6

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✦ Synopsis

The A-ring precursor of 1α,25-dihydroxyvitamin D 3 [(E)-4] has been prepared starting from the (5S)-tertbutyldimethylsiloxy-2-cyclohexenone [(S)-1] via eight steps in 19% overall yield, where a catalytic osmium dihydroxylation which sets the stereochemistry of the hydroxyl group at C 1 and a regioselective protection of the hydroxy group as a TBS-ether are the key steps.

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