BARC/PUB/2015/0544

 
 

Asymmetric synthesis of the constitutive C22-carboxylic acid of macroviracin A

 
     
 
Author(s)

Kanojia, S. V.; Chatterjee, S.; Gamre, S.; Chattopadhyay, S.; Sharma, A.
(BOD)

Source

Tetrahedron, 2015. Vol. 71 (11): pp. 1732-1738

ABSTRACT

An efficient asymmetric synthesis of the C22-trihydroxy fatty acid component of macroviracin A has been developed. The key steps were highly enantioselective (i) lipase-catalyzed acylation, (ii) InCl3-(S)-BINOL mediated allylation, and (iii) asymmetric dihydroxylation (ADH) reaction. The moderate diaster-eoselectivity of the ADH reaction was overridden by converting the resultant diol diastereomers to the required epoxide enantiomer.

 
 
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