Process for preparing allenic prostanoic acid derivatives

Details Process for preparing allenic prostanoic acid derivatives Process for preparing allenic prostanoic acid derivatives

1988-12-13

1990-04-10

Raymond, Richard L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

556441, C07F 718

Patent

active

049162381

ABSTRACT:
This invention relates to a novel process for making an allenic prostanoic acid derivative in the form of a single stereoisomer, or a mixture of stereosiomers, represented by the formula (I): ##STR1## wherein R is lower alkyl, R.sup.1 is a protecting group which can be selectively removed in the presence of R.sup.2, R.sup.2 is an acid-labile, base-stable protecting group, X is --(CH.sub.2).sub.2 --, trans --CH.dbd.CH-- or --C.tbd.C--, Y is --C(R.sup.3)(OR.sup.2)CH.sub.2 --, in which --OR.sup.2 is in the .alpha. or .beta. configuration and R.sup.3 is hydrogen or methyl, Z is alkyl, or phenyl, benzyl or phenoxy each optionally substituted on the phenyl ring, and the wavy lines represent the .alpha. or .beta. configuration with the proviso that when one wavy line is .alpha. the other is .beta..

REFERENCES:
patent: 3879438 (1975-04-01), Crabbe et al.
patent: 3985791 (1976-10-01), Muchowski et al.
patent: 4418206 (1983-11-01), Wren
patent: 4578505 (1986-03-01), Collins et al.
patent: 4600785 (1986-07-01), Cooper et al.
patent: 4689419 (1987-08-01), Collins et al.
patent: 4778904 (1988-10-01), Cooper
Tetrahedron Letters No. 51, pp. 4615-4618, (1985).
J. Am. Chem. Soc., vol. 106, 3368-3370, (1984).

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