Synthesis of the aminocyclitol units of (-)-hygromycin A and methoxyhygromycin from myo-inositol.
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.
Division of Organic Chemistry, National Chemical Laboratory, Dr. Homibhabha Road, Pune-411 008, India.
Bharat P
BP
Gurale
Mysore S
MS
Shashidhar
Rajesh G
RG
Gonnade
D002236:Carbohydrate Conformation; D002934:Cinnamates / Q000138:chemical synthesis* / Q000737:chemistry; D054812:Cyclitols / Q000737:chemistry*; D006921:Hygromycin B / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D007294:Inositol / Q000031:analogs & derivatives / Q000737:chemistry*; D013237:Stereoisomerism
D002934:Cinnamates; D054812:Cyclitols; C575960:methoxyhygromycin; D006921:Hygromycin B; C026273:hygromycin A; D007294:Inositol