Process for making epoxide intermediates

Details Process for making epoxide intermediates Process for making epoxide intermediates

1998-09-04

2000-05-23

Trinh, Ba K.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549561, 560121, 562503, C07D30114

Patent

active

060667516

ABSTRACT:
It has been surprisingly discovered that the disadvantages of the lengthy literature procedures to synthesize 13,14-dihydro prostaglandin A, E, and F derivatives can be overcome using a novel Methyl 7-(2-hydroxy-5-(2-(2-oxiranyl)ethyl)-4-(1,1,2,2 tetramethyl-1-silapropoxy)cyclopentyl) heptanoate intermediate, which can be synthesized from commercially available Methyl 7-[3-(R)-hydroxy-5-oxo-1-cyclopent-1-yl] heptanoate. This novel intermediate can be coupled with oxygen, carbon, sulfur, and nitrogen nucleophiles, in the presence of a base or a Lewis acid, in a ring-opening process to provide 13,14-dihydro prostaglandin A, E, and F derivatives.

REFERENCES:
patent: 3435053 (1969-03-01), Beal et al.
patent: 3505386 (1970-04-01), Babcock et al.
patent: 3776938 (1973-12-01), Bergstrom et al.

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