Formal synthesis of valiolamine from myo-inositol

TitleFormal synthesis of valiolamine from myo-inositol
Publication TypeJournal Article
Year of Publication2011
AuthorsJagdhane, RC, Shashidhar, MS
JournalTetrahedron
Volume67
Issue41
Pagination7963-7970
Date PublishedOCT
ISSN0040-4020
KeywordsAmino sugar, Carbohydrate, Cyclitol, Inositol, Natural product, Valiolamine
Abstract

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.

DOI10.1016/j.tet.2011.08.027
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)3.04
Divison category: 
Organic Chemistry