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

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 di...

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Bibliographic Details
Published in:Tetrahedron 2015-03, Vol.71 (11), p.1732-1738
Main Authors: Kanojia, Seema V., Chatterjee, Sucheta, Gamre, Sunita, Chattopadhyay, Subrata, Sharma, Anubha
Format: Article
Language:English
Subjects:
Antiviral agent
Asymmetric synthesis
Lipase-catalyzed reaction
macroviracin A
Total synthesis
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Summary: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 diastereoselectivity of the ADH reaction was overridden by converting the resultant diol diastereomers to the required epoxide enantiomer. [Display omitted] An enantioconvergent synthesis of the advanced intermediate of macroviracin A has been developed, using enantioselective lipase-catalyzed acylation, asymmetric allylation, and asymmetric dihydroxylation reaction to install the required stereogenic centers. The key reactions proceeded with good to excellent stereoselectivity.
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.01.010