New synthesis of (+/-)-isonucleosides.
[Structure: see text] A novel method for synthesizing isonucleosides, a new class of anti-HIV nucleosides, is described. 2,2-Dimethyl-1,3-dioxan-5-one was converted into a dioxabicyclohexane derivative in six steps. After cleaving the epoxide group with thiophenol, the resulting product was subjected to the Mitsunobu reaction in the presence of a nucleobase to give the desired isonucleoside derivative via migration of the thiophenyl group. Removal of the thiophenyl group under radical conditions followed by deprotection led to the 4'-substituted 2',3'-dideoxyisonucleosides as a racemic mixture.
Yoshimura
Yuichi
Y
Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan. yoshimura@tohoku-pharm.ac.jp
Asami
Kazuhiro
K
Matsui
Hiromitsu
H
Tanaka
Hiromichi
H
Takahata
Hiroki
H
D009705:Nucleosides / Q000138:chemical synthesis*
D009705:Nucleosides