Nucleosides. IX. Synthesis of purine N(3),5'-cyclonucleosides and N(3),5'-cyclo-2',3'-seconucleosides via Mitsunobu reaction as TIBO-like derivatives.
The Mitsunobu reaction was applied to prepare, in one step, purine N(3),5'-cyclonucleosides 10a-d. A subsequent ring opening in the ribose moiety of the resultant N(3),5'-nucleosides by sodium periodate led to the corresponding N(3),5'-cyclo-2',3'-seconucleosides. These products consist of 5-, 6-, and 7-membered tricyclic system which is the basic skeleton of TIBO derivatives, known antiviral agents.
Chen
Grace Shiahuy
GS
School of Pharmacy, College of Medicine, National Taiwan University, Taipei, Taiwan, ROC.
Chen
Chien-Shu
CS
Chien
Tun-Cheng
TC
Yeh
Jun-Yen
JY
Kuo
Chia-Chi
CC
Talekar
Rahul Subhash
RS
Chern
Ji-Wang
JW
D001569:Benzodiazepines / Q000138:chemical synthesis / Q000737:chemistry; D005573:Formycins / Q000737:chemistry; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry; D011684:Purine Nucleosides / Q000138:chemical synthesis*
C476867:4,5,6,7-tetrahydroimidazo-(4,5,1- jk)(1,4)benzodiazepin-2 (1 H)-one; D005573:Formycins; D007093:Imidazoles; D011684:Purine Nucleosides; D001569:Benzodiazepines; C034561:formycin B