Asymmetric synthesis of the constitutive C-22-carboxylic acid of macroviracin A

作者：Kanojia Seema V; Chatterjee Sucheta; Gamre Sunita; Chattopadhyay Subrata; Sharma Anubha^*

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

DOI：10.1016/j.tet.2015.01.010

• Asymmetric synthesis
• Total synthesis
• Antiviral agent
• macroviracin A
• Lipase-catalyzed reaction

An efficient asymmetric synthesis of the C-22-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.

• 出版日期2015-3-18