Tuning Cross-coupling approaches to C3 modification of 3-deazapurines

Authors

Łukasz J. Weseliński, Michigan Technological University
Vagarshak Begoyan, Michigan Technological University
Alexis Ferrier, Michigan Technological University
Marina Tanasova, Michigan Technological UniversityFollow

Document Type

Article

Publication Date

10-20-2017

Department

Department of Chemistry

Abstract

A general approach to C3 modification of purine scaffold through various types of cross-coupling reactions has been established. Tuning substrate electronics and reaction conditions resulted in the development of highly efficient sp²–sp, sp²–sp², and sp²–sp³ cross-coupling conditions for modification of 3-deazaadenine to access C₃-modified adenine and hypoxanthine scaffolds. The optimized methodologies to access the corresponding 3-deazaadenosine phosphoramidites for solid-phase DNA synthesis have been demonstrated.

Publication Title

Women in Organic Chemistry

Recommended Citation

Weseliński, Ł. J., Begoyan, V., Ferrier, A., & Tanasova, M. (2017). Tuning Cross-coupling approaches to C3 modification of 3-deazapurines. Women in Organic Chemistry, 2(10), 7002-7015. http://doi.org/10.1021/acsomega.7b01159
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/1279