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Organopalladium approaches to prostaglandins. : 6. synthesis of Interphenylene Prostaglandin Endoperoxidte Analogs Via Benzylpalladation of Bicyclic Alkenes.

โœ Scribed by Richard C. Larock; Srinivasan Babu


Book ID
108371594
Publisher
Elsevier Science
Year
1987
Tongue
French
Weight
732 KB
Volume
43
Category
Article
ISSN
0040-4020

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๐Ÿ“œ SIMILAR VOLUMES


Organopalladium approaches to prostaglan
โœ Richard C. Larock; Srinivasan Babu ๐Ÿ“‚ Article ๐Ÿ“… 1985 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 145 KB

The reaction of norbornene, norbornadiene and 7-oxanorbornene with methyl 3-(chloromet y phenoxyacetate, (S)-l-octyn-3-01 and 8% Pd(PPh3)4 affords in one step satisfactory yields of the corresponding, first interphenylene PGH2 analogs.

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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.

Organopalladium approaches to prostaglan
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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