Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1982-05-10
1984-05-08
Brust, Joseph P.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
260464, 560121, C07C 6974, C07C12148
Patent
active
044476361
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.,.beta.-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-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: 3828026 (1974-08-01), Burns
patent: 4125556 (1978-11-01), White et al.
Windholz, et al., Tetrahedron Letters, No. 27, pp. 2555-2557 (1967).
Anzeveno Peter B.
White William L.
Brust Joseph P.
The Dow Chemical Company
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