92016-00-7Relevant academic research and scientific papers
General approach to prostanes B1 by intermolecular pauson-khand reaction: Syntheses of methyl esters of prostaglandin B1 and phytoprostanes 16-B1-PhytoP and 9-L1-PhytoP
Vazquez-Romero, Ana,Verdaguer, Xavier,Riera, Antoni
supporting information, p. 1716 - 1725 (2013/04/10)
A synthetic approach to the methyl esters of Prostaglandin B1 and Phytoprostanes 16-B1-PhytoP (PPB1-I) and 9-L 1-PhytoP (PPB1-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. A synthetic approach to prostanes B1 based on Julia olefination of a formylcyclopentenone and an appropriately protected hydroxy sulfone has been developed. Cyclopentenones were prepared by intermolecular Pauson-Khand reaction. Protection of the alcohol functionality of the hydroxy sulfone as a tert-butyl ether proved to be crucial. Copyright
The synthesis of polyunsaturated α,ω-dicarboxylic acids. I. Chemical synthesis of octadecadienedioic acids regioisomeric in double bond positions
Ivanov,Groza,Mal'chenko,Myagkova,Shewe
, p. 481 - 487 (2007/10/03)
Novel compounds, (6Z,9Z)-octadecadienedioic acid, its regioisomers in double bond positions, and their acetylenic precursors, were synthesized. A general approach to the synthesis of a series of ω-hydroxyacetylenic acids in the context of a unique synthetic scheme was suggested.
