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Organopalladium approaches to prostaglandins. 9. Synthesis of a prostaglandin endoperoxide analogue by allylpalladation-ozonolysis of norbornene

โœ Scribed by R.C. Larock; K. Narayanan


Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
477 KB
Volume
44
Category
Article
ISSN
0040-4020

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๐Ÿ“œ SIMILAR VOLUMES


Organopalladium approaches to prostaglan
โœ R.C. Larock; M.H. Hsu; K. Narayanan ๐Ÿ“‚ Article ๐Ÿ“… 1987 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 453 KB

Vinylpalladation of norbornene using vinylmercurial 5 and Li2PdC14 affords the corresponding cis-exo adduct 6 which can be directly carbonylated to methyl ester 7 in 60% overall yield. Reduction to aldehyde 9 and subsequent chain elaboration provides the new prostaglandin endoperoxide analog 12. Epi

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Thlophene-contalnlng prostaglandln endoperoxlde analogs are readily avallable by addltlon of thlenylpalladlum species to blcycllc oleflns and subsequent treatment with alkenyl or alkynyl organometalllcs. Hydrogenation affords blcycllc and trlcycllc prostanolc acid analogs.