Intramolecular Radical Reactions of 5′-O-Modified 2′,3′-Didehydro-2′,3′-Dideoxyuridine Derivatives

Abstract

Radical reactions of 5′-O-(2-bromo-1-methoxy)ethyl- and 5′-O-(2-propynyl)-2′,3′-dideoxy-2′,3′-didehydrouridines were investigated. Both reactions proceeded in a 6-exo-trig manner to give products cyclized regio- and stereospecifically at the 3′-position. The structures of these products were analyzed by X-ray crystallography.

1) Present address: Chemical Analysis Center, Chiba University, 1-33 Yayoicho, Inage-ku, Chiba 263, Japan.

This paper is dedicated to Dr. Yoshihisa Mizuno, one of the founders of nucleic acids chemistry in Japan, on the occassion of his 75th birthday.

Notes

1) Present address: Chemical Analysis Center, Chiba University, 1-33 Yayoicho, Inage-ku, Chiba 263, Japan.

This paper is dedicated to Dr. Yoshihisa Mizuno, one of the founders of nucleic acids chemistry in Japan, on the occassion of his 75th birthday.

Present address: Chemical Analysis Center, Chiba University, 1-33 Yayoicho, Inage-ku, Chiba 263, Japan