6,6-Difluoro-5-hydroxy-4-(3-oxoalk-1-enyl)hexahydro cyclopenta[b

Details 6,6-Difluoro-5-hydroxy-4-(3-oxoalk-1-enyl)hexahydro cyclopenta[b 6,6-Difluoro-5-hydroxy-4-(3-oxoalk-1-enyl)hexahydro cyclopenta[b

1981-09-24

1982-12-07

Jiles, Henry R.

Harness for working animal

549265, C07D307935

Patent

active

043628729

ABSTRACT:
A method is provided for preparing intermediates for use in 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.

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