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Synthesis of the Aminocyclitol Units of (−)-Hygromycin A and Methoxyhygromycin from myo-Inositol

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journal contribution
posted on 06.07.2012, 00:00 by Bharat P. Gurale, Mysore S. Shashidhar, Rajesh G. Gonnade
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.