Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers

Shengyang Wang; Jiansong Sun; Qingju Zhang; Xin Cao; Yachen Zhao; Gongli Tang; Biao Yu

doi:10.1002/anie.201800169

Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers

Angew Chem Int Ed Engl. 2018 Mar 5;57(11):2884-2888. doi: 10.1002/anie.201800169. Epub 2018 Feb 12.

Authors

Shengyang Wang¹, Jiansong Sun², Qingju Zhang¹, Xin Cao¹, Yachen Zhao¹, Gongli Tang¹, Biao Yu¹

Affiliations

¹ State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
² The National Engineering Research Centre for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang, 330022, China.

PMID: 29356246
DOI: 10.1002/anie.201800169

Abstract

The proposed diastereoisomers (1 a-d) together with their C8'-epimers (1 e-h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio- and stereocontrolled gold(I)-catalyzed N-glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3' in amipurimycin should be of opposite configuration.

Keywords: amino acids; antibiotics; glycosylation; gold; natural products.

Publication types

Research Support, Non-U.S. Gov't