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General Approach to Prostanes B 1 by Intermolecular Pauson–Khand Reaction: Syntheses of Methyl Esters of Prostaglandin B 1 and Phytoprostanes 16‐B 1 ‐PhytoP and 9‐L 1 ‐PhytoP
Author(s) -
VázquezRomero Ana,
Verdaguer Xavier,
Riera Antoni
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201442
Subject(s) - sulfone , chemistry , regioselectivity , ether , alkyne , intermolecular force , pauson–khand reaction , sulfoxide , medicinal chemistry , ring (chemistry) , stereochemistry , organic chemistry , molecule , catalysis
A synthetic approach to the methyl esters of Prostaglandin B 1 and Phytoprostanes 16‐B 1 ‐PhytoP (PPB 1 ‐I) and 9‐L 1 ‐PhytoP (PPB 1 ‐II) based on the modified Julia olefination of a formylcyclopentenone and an appropriately protected hydroxy sulfone has been developed. The cyclopentenones were efficiently prepared by intermolecular Pauson–Khand reaction of a (silyloxymethyl)alkyne. The sulfone counterpart was prepared by regioselective ring‐opening of the appropriate chiral epoxides by 2‐mercaptobenzothiazole. The protecting group for the alcohol functionality on the sulfone proved to be crucial. Protection as a tert ‐butyl ether was the best solution, giving better results than a tert ‐butyldimethylsilyl ether.