Acetylenic cyclohexane triol derivatives

Details Acetylenic cyclohexane triol derivatives Acetylenic cyclohexane triol derivatives

1995-05-23

1996-01-30

Siegel, Alan

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

Organic compounds

Oxygen containing

568606, 568670, 556443, C07C 3508, C07F 708

Patent

active

054881838

ABSTRACT:
A synthesis of 1.alpha.-hydroxy-19-nor-vitamin D compounds comprises (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.

REFERENCES:
patent: 5086191 (1992-02-01), DeLuca et al.
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 Attition 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.
Perlman, Kato et al, "Novel Synthesis of 19-Nor-Vitamin D Compounds", Tetrahedron Letters, vol. 32, No. 52, pp. 7663-7666, 1991.

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