A rapid access to chiral alkylidene cyclopentenone prostaglandins involving ring-closing metathesis reaction |
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| Authors: | Robert WeavingEmmanuel Roulland Claude MonneretJean-Claude Florent |
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| Institution: | Laboratoire de Pharmacochimie, UMR 176 CNRS-Institut Curie, Section Recherche, 26, rue d'Ulm, 75248 Paris cedex 05, France |
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| Abstract: | A synthesis of the alkylidene cyclopentenone prostaglandin TEI 9826 has been realized. The synthesis involved the preparation of the chiral 1,5-diene 8 using a stereoselective Claisen rearrangement from the allylic alcohol 6 giving the ester 7 after vinylation. Then a key RCM reaction allowed the preparation of the cyclopentenol 9 which, after oxidation, gave the cyclopentenone 10, precursor of the prostaglandin. |
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