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Issue 8, 2017
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First asymmetric total synthesis of aspergillide D

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Abstract

The first asymmetric total synthesis of a 16-membered macrolide, aspergillide D, is described. The chiral centers of the acid are derived from D-ribose and the alcohol subunit from 1,8-octane diol through Sharpless kinetic resolution, respectively. The other key reactions include Yamaguchi esterification, ring-closing metathesis reaction, and Shiina macrolactonization to construct the fully functionalized macrocycle.

Graphical abstract: First asymmetric total synthesis of aspergillide D

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Article information


Submitted
08 Nov 2016
Accepted
24 Jan 2017
First published
24 Jan 2017

Org. Biomol. Chem., 2017,15, 1863-1871
Article type
Paper

First asymmetric total synthesis of aspergillide D

B. K. Jena, G. S. Reddy and D. K. Mohapatra, Org. Biomol. Chem., 2017, 15, 1863
DOI: 10.1039/C6OB02435A

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