Synthesis of 19-nor vitamin D compounds

Details Synthesis of 19-nor vitamin D compounds Synthesis of 19-nor vitamin D compounds

1992-11-20

1994-01-25

Reamer, James H.

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

Organic compounds

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

556445, 556478, 558115, 568 33, 568 17, C07C40100

Patent

active

052817318

ABSTRACT:
A convergent synthesis of 19-nor-vitamin D compounds, specifically 19-nor-1.alpha.,25-dihydroxyvitamin D.sub.3, is disclosed. The synthesis can also readily be utilized for preparing other 1.alpha.-hydroxylated 19-nor-vitamin D compounds. The key step in the synthesis is a suitable application of Lythgoe's procedure i.e. a Horner-Wittig reaction of the lithium anion of a phosphine oxide with a Windaus Grundmann ketone to give, after any necessary deprotection, the desired 19-nor-vitamin D compound.

REFERENCES:
Sardinas, et al, J. Org. Chem., 51, 1264-1269, 1986.
Toh, et al., J. Org. Chem., 48, 1414-1417, 1983.
Baggiolini, et al. J. Org. Chem., 51, 3098-3108, 1986.
Lythgoe, Chem. Soc. Review, 9, 449-474, 1983.
Lythgoe, et al, J. Chem. Soc. Perkin Trans. I, 590-595, 1978.

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