2002 Fiscal Year Final Research Report Summary
Development of New Silicon Tethers and Their Application to the Synthesis of Anti-HIV Nucleosides
Project/Area Number |
13672203
|
Research Category |
Grant-in-Aid for Scientific Research (C)
|
Allocation Type | Single-year Grants |
Section | 一般 |
Research Field |
Chemical pharmacy
|
Research Institution | HOKKAIDO UNIVERSITY |
Principal Investigator |
SHUTO Satoshi Hokkaido Univ. Grad. School of Pharm. Sci., Associate Prof., 大学院・薬学研究科, 助教授 (70241346)
|
Project Period (FY) |
2001 – 2002
|
Keywords | Silicon tether / Ethynyl group / Radical reaction / Atom transfer / Anti-HIV agent / Nucleoside |
Research Abstract |
A novel radical method for the stereoselective introduction of an ethynyl group using ethynyldimethylsilyl (EDMS) or [2-(trimethylsilyl)ethynyl]dimethylsilyl (TEDMS) as the radical acceptor tethers has been developed. When a solution of EDMS or TEDMS ethers of trans-2-iodoindanoI was treated with Et_3B followed by tetrabutylammonium fluoride in toluene, atom transfer 5-exo-cyclization and subsequent elimination occurred to give cis-2-ethynylindanol in high yield. The method was shown to be useful in the introduction of an ethynyl group in various five and six-membered ring iodohydrins. Furthermore, 2'-deoxy-2'-C-ethynyluridine and cytidine, which were designed as novel anti-HIV nucleoside analogues, were readily synthesized using this method as the key step.
|
Research Products
(12 results)
-
-
-
-
-
-
-
-
-
-
[Publications] S. Shuto, M. Kanazaki, I. Sugimoto, S. Ichikawa, Y. Nagasawa, Y. Ueno, H. Abe, N. Minakawa, M. Sukeda, T. Kodama, M. Nomura, A. Matsuda: "evelopment of new radical reactions with a vinylsilyl group and their application to the synthesis of branched-chain sugar nucleosides"Recent Advances in Nucleosides : Chemistry and Chemotherapy, Ed. By C. K. Chu, Elsevier. 21-55 (2002)
Description
「研究成果報告書概要(欧文)」より
-
-