Prostaglandins and methods for preparing same

Details Prostaglandins and methods for preparing same Prostaglandins and methods for preparing same

1977-02-25

1979-02-27

Gerstl, Robert

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

Organic compounds

Carboxylic acid esters

C07C 6974

Patent

active

041420560

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-transoctene 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:
fiesen et al., Reagents for Organic Synthesis', p. 136 (1967).

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