Recent advances in the synthesis of 4′-truncated nucleoside phosphonic acid analogues

Shen, Guang Huan; Hong, Joon Hee

doi:10.1016/j.carres.2022.108517

Search citation statements

Order By: Relevance

Paper Sections

Select...

Introduction1

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2022

2024

Publication Types

Select...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

(1 citation statement)

References 147 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[6] However, due to the emergence of drug resistance and toxicity, it is imperative to develop new bioactive pyrimidine nucleoside analogues. Therefore, the development of efficient methodologies for the synthesis of chiral isoxazole [7] and carbocyclic pyrimidine nucleoside analogues is highly desirable.…”

Section: Introductionmentioning

confidence: 99%

Lewis Acid Catalyzed (3+2)‐Cycloadditions of Chiral Pyrimidinyl‐Substituted Cyclopropanes with Nitrosoarenes or Silyl Enol Ethers

et al. 2022

View full text Add to dashboard Cite

Chiral isoxazole and carbocyclic pyrimidine nucleoside analogues were synthesized via (3 + 2)-cycloadditions of chiral pyrimidinyl-substituted dimethyl cyclopropanedicarboxylates. In the presence of MgI 2 , (3 + 2)-cycloadditions of chiral pyrimidinyl-substituted cyclopropanes with nitrosoarenes afforded diverse chiral isoxazole pyrimidine nucleoside analogues in up to 78 % yield and 88-96 % ee. Using Nd(OTf) 3 as the catalyst, the annulation reaction with silyl enol ethers generated a series of chiral carbocyclic pyrimidine nucleoside analogues in up to 64 % yield, > 20 : 1 dr, and 87-96 % ee. The proposed methods either reduced or avoided partial racemization.

show abstract

Section: Introductionmentioning

confidence: 99%