SAMARIUM DIIODIDE-INDUCED RADICAL CYCLIZATION OF OXIME ETHER CONNECTED WITH FORMYL GROUP - SYNTHESIS OF 4-PYRIMIDINYLPYRROLIDIN-3-OL AND 4-PURINYLPYRROLIDIN-3-OL NUCLEOSIDE ANALOGS

Authors
MIYABE H KANEHIRA S KUME K KANDORI H NAITO T
Citation
H. Miyabe et al., SAMARIUM DIIODIDE-INDUCED RADICAL CYCLIZATION OF OXIME ETHER CONNECTED WITH FORMYL GROUP - SYNTHESIS OF 4-PYRIMIDINYLPYRROLIDIN-3-OL AND 4-PURINYLPYRROLIDIN-3-OL NUCLEOSIDE ANALOGS, Tetrahedron, 54(22), 1998, pp. 5883-5892
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
22
Year of publication
1998
Pages
5883 - 5892
Database
ISI
SICI code
0040-4020(1998)54:22<5883:SDRCOO>2.0.ZU;2-A
Abstract
SmI2-induced 5-exo-trig radical cyclization of oxime ether intramolecu larly connected with the formyl group was found to be particularly eff ective for preparing cyclic trans-amino alcohol in good chemical yield with a high degree of stereoselectivity. Ils successful application t o the synthesis of a novel class of 4-pyrimidinyl- and 4-purinylpyrrol idin-3-ol nucleoside analogues is also described. (C) 1998 Elsevier Sc ience Ltd. All rights reserved.