TY - JOUR
T1 - Chemoenzymatic stereoconvergent synthesis of 3-O-benzoyl azidosphingosine
AU - Compostella, Federica
AU - Franchini, Laura
AU - Giovenzana, Giovanni Battista
AU - Panza, Luigi
AU - Prosperi, Davide
AU - Ronchetti, Fiamma
N1 - Funding Information:
The authors thank the MIUR, the University of Piemonte Orientale and the University of Milano for financial support.
PY - 2002/5/15
Y1 - 2002/5/15
N2 - The synthesis of 3-O-benzoyl azidosphingosine 1 through a stereoconvergent approach is described. Nucleophilic addition of the Grignard reagent of 1-pentadecyne to cyclohexylidene-D-glyceraldehyde results in a mixture of diastereoisomeric propargylic alcohols. Subsequent enzymatic separation of these diastereoisomers, mediated by lipase from Candida antarctica, Mitsunobu inversion on the wrong diastereoisomer and extremely efficient introduction of azide using a chloromesylate leaving group affords the title compound in 30% overall yield.
AB - The synthesis of 3-O-benzoyl azidosphingosine 1 through a stereoconvergent approach is described. Nucleophilic addition of the Grignard reagent of 1-pentadecyne to cyclohexylidene-D-glyceraldehyde results in a mixture of diastereoisomeric propargylic alcohols. Subsequent enzymatic separation of these diastereoisomers, mediated by lipase from Candida antarctica, Mitsunobu inversion on the wrong diastereoisomer and extremely efficient introduction of azide using a chloromesylate leaving group affords the title compound in 30% overall yield.
UR - http://www.scopus.com/inward/record.url?scp=0037094745&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(02)00201-X
DO - 10.1016/S0957-4166(02)00201-X
M3 - Article
SN - 0957-4166
VL - 13
SP - 867
EP - 872
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 8
ER -