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A short synthesis of (−)-prostaglandin E1

✍ Scribed by T Tanaka; T Toru; N Okamura; A Hazato; S Sugiura; K Manabe; S Kurozumi; M Suzuki; T Kawagishi; R Noyori

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
157 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

Prostaglandin El has been prepared from (fi)-4-t-butyldimethylsiloxy-2-cyclopentenone by using as a key operation the tandem organocopper conjugate additionlnitroolefin Michael trapping of the resulting enolate intermediate. Regiospecific trapping with electrophiles of enolates generated from 2-cyclenones and lithium diorganocuprates provides a useful tool for the synthesis of 2,3-difunctionalized cyclic ketones. 2 In certain cases, replacement of the organocuprate complexes by organocopper reagents of type RCu[ P(n-C4H9)3]n (p = 2 or 3, empirical formula)3 results in remarkable increase in the efficiency and selectivity of the three-component coupling processes. 495

We found that an enolate which was generated by the reaction of 2-cyclopentenone or its

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## Abstract This report describes an efficient stereoselective synthesis of [11β‐^3^H]prostaglandin E~1~ ([11β‐^3^H]PGE~1~). The key multiply protected 11‐keto intermediate was prepared in only three steps from PGE~1~. Reduction of the ketone function at C‐11 with sodium borodeuteride and sodium bo