Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1978-06-19
1979-03-27
Torrence, Dolph H.
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
260465D, 560121, 560122, C07C 6974, C07C12148
Patent
active
041465539
ABSTRACT:
Improved procedures and intermediates for synthesizing 11-deoxyprostaglandins wherein trans-2,3-dicarbomethoxycyclopentanone is prepared by the novel kinetically-controlled cyclization of 1,2,4-tricarbomethoxybutane using a dispersion of sodium hydride in dry p-xylene. Selective alcoholysis of the 2-position carbomethoxy group with benzyl alcohol, followed by alkylation allows for a wide range of upper side chains to be introduced at the 2-position of the cyclopentanone ring. The unwanted carbobenzyloxy group at the 2-position can then be removed easily by controlled hydrogenolysis followed by decarboxylation. This procedure allows for simultaneous epimerization of the 2-position side chain to the desired trans-configuration, relative to the carbomethoxy group in the 3-position, as well as for reduction of the 2-hexynyl moiety of the side chain to the desired cis-olefinic group of the E.sub.2 -type 11-deoxyprostaglandins, or through total reduction to the alkane upper side chain of E.sub.1 -type prostaglandin analogs. Modification thereafter of the carbonyl group at the 3-position of the cyclopentanone ring by a variety of reagents allows introduction of the lower side chain present in the prostaglandins themselves or a variety of other side chains derived from the 3-carboxy-, 3-hydroxymethyl- or 3-aldehyde-substituted cyclopentanone ring. From the latter, 11-deoxyprostaglandins can be prepared by known procedures.
REFERENCES:
patent: 4045465 (1977-08-01), Hess et al.
patent: 4055593 (1977-10-01), Weinshenker et al.
Johnson Francis
White William L.
The Dow Chemical Company
Torrence Dolph H.
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