Synthesis of the aminocyclitol units of (-)-hygromycin a and methoxyhygromycin from myo-inositol

TitleSynthesis of the aminocyclitol units of (-)-hygromycin a and methoxyhygromycin from myo-inositol
Publication TypeJournal Article
Year of Publication2012
AuthorsGurale, BP, Shashidhar, MS, Gonnade, RG
JournalJournal of Organic Chemistry
Volume77
Issue13
Pagination5801-5807
Date PublishedJUL
ISSN0022-3263
Abstract

Concise and efficient syntheses of the aminocyclitol cores of hygromycin A (HMA) and methoxyhygromycin (MHM) have been achieved starting from readily available myo-inositol. Reductive cleavage of myo-inositol orthoformate to the corresponding 1,3-acetal, stereospecific introduction of the amino group via the azide, and resolution of a racemic cyclitol derivative as its diastereomeric mandelate esters are the key steps in the synthesis. Synthesis of the aminocyclitol core of hygromycin A involved chromatography in half of the total number of steps, and the aminocyclitol core of methoxyhygromycin involved only one chromatography.

DOI10.1021/jo300444b
Type of Journal (Indian or Foreign)Foreign
Impact Factor (IF)4.564
Divison category: 
Center for Material Characterization (CMC)
Organic Chemistry