Synthesis of 2'-aminouridine derivatives as an organocatalyst for Diels-Alder reaction

Hideaki Wakamatsu; Moeko Itoh; Yoshihiro Natori; Yuichi Yoshimura

doi:10.1080/15257770.2019.1646917

Synthesis of 2'-aminouridine derivatives as an organocatalyst for Diels-Alder reaction

Nucleosides Nucleotides Nucleic Acids. 2020;39(1-3):365-383. doi: 10.1080/15257770.2019.1646917. Epub 2019 Jul 30.

Authors

Hideaki Wakamatsu¹, Moeko Itoh¹, Yoshihiro Natori¹, Yuichi Yoshimura¹

Affiliation

¹ Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai, 981-8558, Japan.

PMID: 31361181
DOI: 10.1080/15257770.2019.1646917

Abstract

To develop a novel asymmetric organocatalyst based on a ribonucleoside skeleton, we designed and synthesized 2'-aminouridine derivatives. The synthesized 2'-aminouridines having bulky substituents at both base and sugar moieties could catalyze the Diels-Alder reaction between cinnamaldehyde and cyclopentadiene. However, the optical purities of the resulting products were unexpectedly low.

Keywords: 2′-aminonucleoside; Diels-Alder reaction; Lithiation; Suzuki-Miyaura coupling; organocatalyst.

MeSH terms

Catalysis
Chemistry Techniques, Synthetic*
Cycloaddition Reaction*
Molecular Structure
Structure-Activity Relationship
Uridine / analogs & derivatives*
Uridine / chemical synthesis*

Substances

Uridine