Radical-based transformation of vicinal diols to olefins via thioxocarbamate derivatives: a simple approach to 2',3'-didehydro-2',3'-dideoxynucleosides
Makoto Oba, Mitsuteru Suyama, Atsushi Shimamura and Kozaburo Nishiyama*
*Department of Material Science and Technology, Tokai University, 317
Nishino, Numazu, Shizuoka 410-0395, Japan, Email:
nishiyam
wing.ncc-u-tokai.ac.jp
M. Oba, M. Suyama, A. Shimamura, K. Nishiyama, Tetrahedron Lett., 2003, 44, 4027-4029.
DOI: 10.1016/S0040-4039(03)00847-5
see article for more reactions
Abstract
Bis-O-thioxocarbamate derivatives of vicinal diols are reduced with tris(trimethylsilyl)silane in the presence of azobisisobutyronitrile to afford the corresponding olefins in good yields. 2',3'-didehydro-2',3'-dideoxy analogs of adenosine, guanosine, inosine, cytidine and uridine were prepared.
see
article for more examples
Radical-based deoxygenation of aliphatic alcohols via thioxocarbamate derivatives
M. Oba, K. Nishiyama, Tetrahedron, 1994, 50, 10193-10200. DOI: 10.1016/S0040-4020(01)81751-8
Key Words
Barton-McCombie reaction, Tris(trimethylsilyl)silane
ID: J72-Y2003-780
