Method for preparing 10,10-difluoro prostacyclins

Details Method for preparing 10,10-difluoro prostacyclins Method for preparing 10,10-difluoro prostacyclins

1980-12-15

1982-03-02

Jiles, Henry R.

Harness for working animal

542429, 26034622, C07D307935

Patent

active

043179061

ABSTRACT:
A method is provided for preparing compounds of the formulae ##STR1## wherein A may be --C.dbd.C-- or --C.tbd.C--, by reducing an epoxy lactone of the structure ##STR2## to form the corresponding epoxy hemiacetal, reacting the epoxy hemiacetal with a silyl compound to form an epoxy silyl acetal, reacting the epoxy silyl acetal with an acetylenic derivative to form a silyl acetal, removing the silyl protecting group to form a hemiacetal, reacting the hemiacetal compound with an appropriate Wittig reagent to form a protected difluoro PGF.sub.2.alpha. type compound, removing the protecting group, reacting the difluoro PGF.sub.2.alpha. with an iodine compound to form an iodoether and reacting the iodoether with a base to form the desired compounds. The compounds may be used, e.g., to prevent the aggregation of blood platelets.
Novel intermediates produced in the above method 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.
Fried et al., Proc. Natl. Acad. Sci. 74, 2199-2203, (1977).

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