Precursors and synthesis of d1-(methyl)-16,16-(dimethyl)-11-alpha, 15-alpha, beta-dihydroxy-9-oxo-2,13,-trans, trans-prostadienoates
AssigneeAmerican Cyanamid Company
InventorMiddleton B. Floyd, Jr.
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AssigneeAmerican Cyanamid Company
InventorMiddleton B. Floyd, Jr.
Estimating the term…
Novel compounds are disclosed of the classes: ##STR1## wherein the subscript n is an integer from 3-5, inclusive, R.sub.1 is hydrogen or R.sub.2 ; R.sub.2 and R.sub.3 consist essentially of C.sub.1 -C.sub.6 alkyl and R.sub.2 may be the same as or different from R.sub.3, and wherein Aryl consists essentially of phenyl and phenyl substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, and trifluoromethyl; (b) derivatives of furan having the formula ##STR2## wherein R.sub.4 consists essentially of hydrogen and C.sub.1 -C.sub.6 alkyl, and W is either carbonyl or carbinol; and (c) cyclopentenonyl compounds having the formulas ##STR3## wherein R.sub.5 consists essentially of hydrogen and C.sub.1 -C.sub.6 alkyl, P.sub.1 is hydrogen or a protective group, Y is either ##STR4## A new process is disclosed for preparing 1-(methyl)-16,16-(dimethyl)-11-alpha-15-alpha-dihydroxy-9-oxo-2,13,trans, trans-prostadienoate, and congeners thereof, including racemic mixtures.
Optically active compounds of the formula ##STR18## and a racemic mixture thereof, wherein n is an integer from 3-5 inclusive, R.sub.5 is selected from the class consisting of hydrogen and C.sub.1 -C.sub.6 lower alkyl, P.sub.1 is hydrogen or P.sub.2, and P.sub.2 is a protective group stable to 1,4 conjugate addition conditions and wherein --Y-- is a divalent moiety selected from the class consisting of trans-(CH.dbd.CH--) and ##STR19## wherein Aryl is selected from the class consisting essentially of phenyl and phenyl substituted with halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or trifluoromethyl.
Dependencies are inferred from the claim text.