15-Deoxy-PGE.sub.1 and method for preparing same

Details 15-Deoxy-PGE.sub.1 and method for preparing same 15-Deoxy-PGE.sub.1 and method for preparing same

1972-01-26

1977-06-21

Gerstl, Robert

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

195 30, 2603458, 260348R, 260468L, 260468K, 260514D, 260514K, 260586R, 424305, 424317, C07C17700

Patent

active

040311295

ABSTRACT:
Racemic 15-deoxy, 11,15-deoxy and other prostaglandins and methods for preparing the same. The initial reactant is lithium cyclopentadiene which is reacted with ethyl-7-bromoheptanoate to give the alkylated diene which in turn is oxygenated to a mixture of hydroxycyclopentenones. 2-(6'-carboethoxyhexyl)-4-hydroxy-cyclopenten-1-one is chromatographically recovered from the mixture and reacted with dihydropyran to give the tetrahydropyranyl ether which is then reacted with 1-lithium-1-trans-octene in the presence of tri-n-butylphosphine-copper iodide to produce racemic 15-deoxy-prostaglandin E.sub.1 ethyl ester which is chromatographically recovered. The ester is converted to the corresponding prostaglandin by the action of an esterase-producing microorganism.

REFERENCES:
samuelsson, J.A.C.S. 87, 3011 (1965).
Pappo et al., Tetrahedron Letters, 2627 (1972).
House et al., J.O.C. 31, 3128 (1966).

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