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A facile synthesis of (−)-prostaglandin E1 via a three-component coupling process

✍ Scribed by M. Suzuki; T. Kawagishi; T. Suzuki; R. Noyori

Publisher
Elsevier Science
Year
1982
Tongue
French
Weight
307 KB
Volume
23
Category
Article
ISSN
0040-4039

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✦ Synopsis

A very short synthesis of choral prostaglandln El methyl ester 1s described.. Although a number of efflclent synthetic routes to prostaglandlns (PGs) have been explored, 495 the three-component couphng process , VIZ., consecutive lntroductlon of the two side-chans to 4hydroxy-Z-cyclopentenone, 1s evidently the simplest converging synthesis. 5 The major obstacles to ths attractive route have been the difficulty in the control of absolute stereochemlstrles at C-11 and C-15 (PG numbering) and lack of the rehable recipes whch allow reglospeclflc vlcinal carbacondensation 6 with Z-cyclopentenones. Now with efficient methods for the enantloselective reduction of a, B-unsaturated ketones7and nucleophlhclelectrophlhc vlclnal carba-condensation of enones secured, this strategy holds considerable promise as a straghtforward entry to various pnmary PGs and their analogues. Described herein 1s a very short synthesis of PGEl methyl ester m optically active form.

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