Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1981-01-30
1982-01-19
Jiles, Henry R.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
542429, 560120, 568819, C07D307935
Patent
active
043116442
ABSTRACT:
A method is provided for preparing intermediates for use in 10,10-difluoro prostacyclin syntheses which method includes the steps of aceylating ketopinic acid or its acid halide to form the corresponding ketopinoyl diene ester intermediate, subjecting the diene ester to a Diels-Alder reaction by reacting same with cyclopentendione, subjecting the resulting chiral ester intermediate to a fluorination and reduction to form the corresponding chiral ester diol intermediate, subjecting the diol to solvolysis to form the chiral triol intermediate, hydroxylating the chiral triol to form a pentol intermediate, subjecting the pentol to a ring cleavage to form the difluoro dihydroxy prostacyclin intermediate ##STR1## and subjecting same to a Wittig reaction to form the difluoro dihydroxy prostacyclin intermediate ##STR2## All of the above-mentioned intermediates are novel compounds and thus are also provided.
REFERENCES:
Fried et al., "10,10-Difluoro-1,3-dehydroprostacyclin: A Chemically and Metabolically Stabilized Potent Prostacyclin", J. Med. Chem. 1980, 23, 234-237.
Fox Rita T.
Haslanger Martin F.
Moniot Jerome L.
Sprague Peter W.
Dentz Bernard
E. R. Squibb & Sons Inc.
Jiles Henry R.
Levinson Lawrence S.
Rodney Burton
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