Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal
Patent
1983-11-02
1985-07-30
Brust, Joseph Paul
Chemistry of carbon compounds
Miscellaneous organic carbon compounds
C-metal
560121, 560122, C07C12148
Patent
active
045320810
ABSTRACT:
Improved procedures and intermediates for synthesizing 11-deoxyprostaglandins wherein trans-2,3-dicarbomethoxycyclopentanone is subjected to a novel alcoholysis with .beta.,.beta.,.beta.-trichloroethanol to substitute a .beta.,.beta.,62 -trichlorocarboethoxy group at the 2-position followed by alkylation to allow for a wide range of upper side chains to be introduced at the 2-position of the cyclopentanone ring. The unwanted .beta.,.beta.,.beta.-trichlorocarboethoxy group at the 2-position can then be removed easily by a zinc induced elimination-decarboxylation sequence. Base catalyzed epimerization of the 2-position side chain to the desired trans-configuration, relative to the carbomethoxy group in the 3-position, is followed by partial reduction of the 2-hexynyl moiety of the side chain to the desired cis-olefinic group of the E.sub.2 -type 11-dioxyprostaglandins, 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.
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Windholz, et al., Tetrahedron Letters, No. 27, pp. 2555-2557, (1967).
Anzeveno Peter B.
White William L.
Brookens Ronald G.
Brust Joseph Paul
Nesbitt Stephen L.
Street Gary D.
The Dow Chemical Company
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