Intermediates for 10,10-difluoroprostacyclins

Details Intermediates for 10,10-difluoroprostacyclins Intermediates for 10,10-difluoroprostacyclins

1981-10-05

1982-07-27

Jiles, Henry R.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

542429, 549215, 549458, C07D307935, C07D30777

Patent

active

043417108

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.
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.

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