Organopalladium approaches to prostaglandins. 1. Synthesis of thiophene-containing prostaglandin endoperoxide analogs via thienylpalladation of bicycle olefins
โ Scribed by R.C. Larock; D.R. Leach; S.M. Bjorge
- Publisher
- Elsevier Science
- Year
- 1982
- Tongue
- French
- Weight
- 216 KB
- Volume
- 23
- Category
- Article
- ISSN
- 0040-4039
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โฆ Synopsis
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.
๐ SIMILAR VOLUMES
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
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.