Intermediates in the preparation of 19-nor vitamin D compounds

Details Intermediates in the preparation of 19-nor vitamin D compounds Intermediates in the preparation of 19-nor vitamin D compounds

1995-03-27

1996-06-11

Prior, Kimberly J.

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

Organic compounds

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

549214, 549414, 549415, 549416, 549420, 549421, 549429, 549472, 549473, 549475, 556437, 556443, 568445, 568612, 568665, 568819, C07C40100

Patent

active

055257453

ABSTRACT:
The invention describes intermediates for use in the synthesis of 1.alpha.-hydroxy-19-nor-vitamin D compounds. The intermediates have the following formula: ##STR1## The disclosed process includes (a) the construction of a 5,8-diol-6-yne intermediate by joining ring-A and ring-C/D portions of the desired end product via the condensation of an acetylenic derivative containing the C/D-ring portion of the desired end product with a cyclic dihydroxy ketone representing the A-ring of the desired end product; (b) the partial reduction of the 6,7 acetylenic triple bond linkage between the A and C/D ring portions to obtain a 5,8-diol-6-ene intermediate; and (c) the reductive removal of the 5,8-oxygen functions to generate the required 5,7-diene end product from which the desired 7-trans(7E)-isomer is purified directly, or after optional double bond isomerization of the 7-cis(7Z)-isomer employing a novel thiophenol-promoted isomerization step.

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Solladie and Hutt "Total Synthesis of Dihydroxyvitamin DHV.sub.3 and Dihydrotachysterol DHT.sub.3 ", J. Org. Chem. 1987, 52, pp. 3560-3566.
Walborsky and Wust, "Titanium-Induced Reductive Elimination. Syntheses of 1,3-Dienes", J. Am. Chem. Soc. 1982, 104, 5807-5808.
Imamoto, Tsuneo et al, "Organocerium Reagents. Nuclephilic Addition to Easily Enolizable Ketones", Tetrahedron Letters, vol. 25, NO. 38, pp. 4233-4236, 1984.
Perlman, Kato et al, "1.alpha.,25-Dihydroxy-19-Nor-Vitamin D.sub.3, A Novel Vitamin D-Related Compound With Potential Therapeutic Activity" Tetrahedron Letters, vol. 31, No. 13, pp. 1823-1824, 1990.
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