The Acetoxyfulvene Synthesis of Prostaglandins: A New, Versatile Synthesis of dl-PGF1δ, dl-PGF2α, dl-PGE1 and dl-PGE2 from a Common Intermediate

Autor:	K. B. Mallion, E. R. H. Walker
Rok vydání:	1975
Předmět:	chemistry.chemical_classification chemistry.chemical_compound chemistry Double bond Bicyclic molecule Hydrogenolysis Stereochemistry Organic Chemistry Synthon Benzyl group Prostaglandin a Cyclopentane Ring (chemistry)
Zdroj:	Synthetic Communications. 5:221-226
ISSN:	1532-2432 0039-7911
Popis:	In the Corey1 synthesis of prostaglandins and in our recently published modifications2,3 a synthon containing carbon atoms 14 to 20θ is first added to a bicyclic intermediate (C-6 to C-13) and completion of the prostaglandin skeleton by addition of a second synthon containing carbon atoms 1 to 5 forms a subsequent step. In a modification4,5 of the Corey synthesis1 PGF1α and PGE1 were made by reversing the order in which these two synthons were added to the cyclopentane ring (C-6 to C-13). The major limitation of this modified route4,5 is that it is restricted to the preparation of prostaglandins of the 1-series,‡ because hydrogenolysis of the benzyl group of the intermediate ester (1) reduces the C-5, C-6 double bond to form the saturated alcohol (2), which cannot be converted into prostaglandins of the 2-series‡.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::29659466e7793145c51f5a81b9aff833 https://doi.org/10.1080/00397917508064114 Zobrazit plný text záznamu