Preparation of 1.alpha., 24-dihydroxyvitamin D analogs

Details Preparation of 1.alpha., 24-dihydroxyvitamin D analogs Preparation of 1.alpha., 24-dihydroxyvitamin D analogs

1992-11-04

1993-09-21

Siegel, Alan

Organic compounds -- part of the class 532-570 series

Organic compounds

9,10-seco-cyclopentanohydrophenanthrene ring system or...

C07J 900

Patent

active

052471047

ABSTRACT:
A synthesis of 1.alpha.,24(R)- and 1.alpha.,24(S)-dihydroxy-22(E)-dehydrovitamin D.sub.3 compounds. This process involves two major operations, namely, (a) the attachment of the required side chain to an existing vitamin D-22-aldehyde derivative to obtain an enone derivative as an intermediate, and (b) the stereoselective reduction of the ketone group of said enone intermediate to obtain the desired 24(R)- and 24(S)-hydroxyvitamin D compounds. The vitamin D enone derivatives generated as intermediates in the process are also new compounds.

REFERENCES:
patent: 4588528 (1986-05-01), DeLuca et al.
patent: 4847012 (1989-07-01), DeLuca et al.
patent: 4866048 (1989-09-01), Calverley et al.
Hiroshi Sai et al, Synthesis and Biological Activity of (22,24R)-and (22E,24S)-1.alpha.,24-Dihydroxy-22-dehydrovitamin D3, Chem. Pharm. Bull. vol. 32, pp. 3866-3872 (1984).

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