Process for the preparation of prostaglandin F.sub.2.sub..alpha.

Details Process for the preparation of prostaglandin F.sub.2.sub..alpha. Process for the preparation of prostaglandin F.sub.2.sub..alpha.

1974-05-23

1976-07-20

Gerstl, Robert

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260 24R, 2603462R, 260413, 260468D, 260520C, C07C17700

Patent

active

039706923

ABSTRACT:
Prostaglandin F.sub.2.sub..alpha. and analogs thereof of the formula ##SPC1##
Wherein one of R.sub.1 and R.sub.2 is hydroxy and the other is H or CH.sub.3, R.sub.3 is the remainder of the lower side chain and X is the remainder of the upper side chain thereof are produced in two steps from a 3-acyloxy mono ester of a lactone of the formula ##SPC2##
Wherein R.sub.1, R.sub.2 and R.sub.3 have the values given below, by reacting the lactone with excess diisobutylaluminum hydride and reacting the thus-produced ketol, in the presence of strong anhydrous base, with a Wittig reagent of the formula Ph.sub.3 P=CH--X--COOH wherein Ph is a phenyl group and X has the values given above.

REFERENCES:
fiezen et al., Reagents for Organic Synthesis, pp. 261-262, 621-622, 123842, (1967).
Corey et al., JACS, 92, 397, (1970).
Corey, Proceedings of the Robert A. Welsh Foundation, Conference on Chemical Research XII, Organic Synthesis, 1969, p. 76.

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