Issue 57, 2022
From the journal:

Chemical Communications

Total synthesis of pseudouridimycin and its epimer via Ugi-type multicomponent reaction†

Ryotaro Okawa,a   Courtney C. Aldrichbc  and  Satoshi Ichikawa ORCID logo *abd  

* Corresponding authors

a Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan
E-mail: ichikawa@pharm.hokudai.ac.jp

b Global Station for Biosurfaces and Drug Discovery, Global Institution for Collaborative Research and Education (GI-CoRE), Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan

c Department of Medicinal Chemistry, Minnesota University, 8-123 Weaver-Densford Hall 308 Harvard St. SE, Minneapolis, MN 55455, USA

d Center for Research and Education on Drug Discovery, Faculty of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan

Abstract

A total synthesis of pseudouridimycin (1) was accomplished featuring an unusual oxime Ugi-type multicomponent condensation to simultaneously construct the dipeptide moiety of this peptidyl nucleoside antibiotic. In this synthetic route 1 is readily accessible via a longest linear sequence of 9 synthetic steps from pseudouridine. This strategy can be applicable to a variety of pseudouridimycin analogues.

Graphical abstract: Total synthesis of pseudouridimycin and its epimer via Ugi-type multicomponent reaction

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Article information

DOI
https://doi.org/10.1039/D2CC02442J
Article type
Communication
Submitted
02 May 2022
Accepted
16 Jun 2022
First published
17 Jun 2022

Chem. Commun., 2022,58, 7956-7959

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Total synthesis of pseudouridimycin and its epimer via Ugi-type multicomponent reaction

R. Okawa, C. C. Aldrich and S. Ichikawa, Chem. Commun., 2022, 58, 7956 DOI: 10.1039/D2CC02442J

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