Process for preparation of calcitriol lactone and related interm

Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...

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552653, C07D30733

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active

053548728

ABSTRACT:
A process for synthesizing (23S,25R)-calcitriol lactone and related Vitamin D analogs comprises reacting protected enantiomerically pure glycidol or 2-alkylglycidol with protected De-A,B-8.beta.-hydroxy-24-nor-cholan-23-al, removing the protective groups from the epimeric product mixture and separating the epimers, to give a hydrindane tetrol product, followed by oxidation and protection of the hydrindane tetrol product, reacting the tetrol product with the lithium salt of (3S)-(3.alpha.,5.beta.,Z)-2-(2-methylene-3,5-bis-((1,1-dimethylethyl)dimet hylsilyloxy)cyclohexy lidene)ethyl diphenyl phosphine oxide and removing the final protective groups. Certain intermediate compounds also show biological activity as angiostatic agents.

REFERENCES:
Seino et al., S. Drugs of the Future, vol. 17, pp. 655-659 (1992).
Hatakeyama et al., J. Chem. Soc., Chem. Commun., pp. 1229-1231 (1992).
Yamamoto et al., J. Org. Chem., vol. 57, pp. 33-39 (1992).
Johnson et al. J. Org. Chem., vol. 50, pp. 2598-2600 (1985).
Wovkulich et al., J. Org. Chem., vol. 48, pp. 4433-4436 (1983).

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