Synthesis of the aminocyclitol units of (-)-hygromycin a and methoxyhygromycin from myo-inositol
Title | Synthesis of the aminocyclitol units of (-)-hygromycin a and methoxyhygromycin from myo-inositol |
Publication Type | Journal Article |
Year of Publication | 2012 |
Authors | Gurale, BP, Shashidhar, MS, Gonnade, RG |
Journal | Journal of Organic Chemistry |
Volume | 77 |
Issue | 13 |
Pagination | 5801-5807 |
Date Published | JUL |
ISSN | 0022-3263 |
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. |
DOI | 10.1021/jo300444b |
Type of Journal (Indian or Foreign) | Foreign |
Impact Factor (IF) | 4.564 |
Divison category:
Center for Material Characterization (CMC)
Organic Chemistry