Organopalladium approaches to prostaglandins. 3. Synthesis of bicyclic and tricyclic 7-oxaprostaglandin endoperoxide analogs via oxypalladation of norbornadiene
โ Scribed by Larock, Richard C.; Leach, Douglas R.
- Book ID
- 126935007
- Publisher
- American Chemical Society
- Year
- 1984
- Tongue
- English
- Weight
- 644 KB
- Volume
- 49
- Category
- Article
- ISSN
- 0022-3263
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๐ SIMILAR VOLUMES
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.
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