%0 Journal Article %J Tetrahedron %D 2011 %T Formal synthesis of valiolamine from myo-inositol %A Jagdhane, Rajendra C. %A Shashidhar, Mysore S. %K Amino sugar %K Carbohydrate %K Cyclitol %K Inositol %K Natural product %K Valiolamine %X

An efficient formal synthesis of racemic valiolamine starting from readily available myo-inositol is reported. In all the synthetic steps only one regioisomer is formed, which circumvents laborious purification of products. Regioselective benzylation of myo-inositol orthoformate, super-hydride mediated deoxygenation of a cyclitol derivative and stereoselective addition of dichloromethyllithium to an inosose are the key reactions in the synthesis. (C) 2011 Elsevier Ltd. All rights reserved.

%B Tetrahedron %I PERGAMON-ELSEVIER SCIENCE LTD %C THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND %V 67 %P 7963-7970 %8 OCT %G eng %N 41 %3

Foreign

%4 3.04 %R 10.1016/j.tet.2011.08.027