First asymmetric total synthesis of aspergillide D

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 esterific...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017-02, Vol.15 (8), p.1863-1871
Main Authors: Jena, Bighnanshu K, Reddy, G Sudhakar, Mohapatra, Debendra K
Format: Article
Language:English
Subjects:
Kinetics
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
Ribose - chemistry
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Summary: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.
ISSN:1477-0520
1477-0539
DOI:10.1039/c6ob02435a