Title of article :
First Enantioselective Synthesis of (-)-(2S,6S)-(6-Ethyltetrahydropyran2-yl)formic Acid
Author/Authors :
Miranda، Leandro S. M. نويسنده , , Meireles، Bruno A. نويسنده , , Costa، Jeronimo S. نويسنده , , Pereira، Vera. L. P. نويسنده , , Vasconcellos، Mario L. A. A. نويسنده ,
Issue Information :
روزنامه با شماره پیاپی سال 2005
Abstract :
We describe in this letter the first enantioselective synthesis of (-)-(2S,6S)(6-ethyltetrahydropyran-2-yl)formic acid (2) in five steps (30% overall yield, 87% ee), from the commercial chiral template (R)-2,3isopropylideneglyceraldehyde (4). The two stereogenic centers in 2 were controlled by diastereoselective Barbier allylation of 4 in aqueous media and an efficient Prins cyclization reaction between 5 with propanal.
Keywords :
antinociceptive activity , Prins cyclization , Barbier reaction , enantioselective synthesis , tetrahydropyran , (R)-2,3-O-isopropylideneglyceraldehyde
