First asymmetric total synthesis of aspergillide D. Issue 8 (6th February 2017)

• Record Type: Journal Article
• Authors: Jena, Bighnanshu K.; Reddy, G. Sudhakar; Mohapatra, Debendra K.
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 8(2017)
• Page Start: 1863
• Page End: 1871
• Publication Date: 2017-02-06
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob02435a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The first asymmetric total synthesis of aspergillide D was achieved in a longest linear sequence of 18 steps following Sharpless resolution, Yamaguchi esterification, RCM reaction and Shiina macrolactonization. Abstract : The first asymmetric total synthesis of a 16-membered macrolide, aspergillide D, is described. The chiral centers of the acid are derived fromd -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.