Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers

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 b...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-03, Vol.57 (11), p.2884-2888
Main Authors: Wang, Shengyang, Sun, Jiansong, Zhang, Qingju, Cao, Xin, Zhao, Yachen, Tang, Gongli, Yu, Biao
Format: Article
Language:English
Subjects:
Aldehydes
Amino acids
Antibiotics
Configurations
Diastereoisomers
Fungicides
Glycosylation
Gold
natural products
NMR
Nuclear magnetic resonance
Nucleosides
Sugar
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. All in the configuration: The proposed diastereoisomers and the relevant C8′ epimers of amipurimycin, a unique peptidyl nucleoside antibiotic, have been synthesized for the first time. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3′ in amipurimycin should be in fact of opposite configuration.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201800169