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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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Publication details

The article was received on 08 Nov 2016, accepted on 24 Jan 2017 and first published on 24 Jan 2017


Article type: Paper
DOI: 10.1039/C6OB02435A
Citation: Org. Biomol. Chem., 2017,15, 1863-1871
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    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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