Synthesis of L-cyclopentenyl nucleosides using ring-closing metathesis and palladium-mediated allylic alkylation methodologies

被引：15

作者：

Agrofoglio, LA

Amblard, F

Nolan, SP

Charamon, S

Gillaizeau, I

Zevaco, TA

Guenot, P

机构：

[1] Univ Orleans, CNRS, UFR Sci, UMR 6005,Inst Chim Organ & Analyt, F-45067 Orleans, France

[2] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA

[3] Forschungszentrum Karlsruhe, Inst Tech Chem, Bereich Chem Phys Verfahren, D-7601 Karlsruhe, Germany

[4] Univ Rennes 1, CRMPO, F-35042 Rennes, France

来源：

TETRAHEDRON | 2004年 / 60卷 / 38期

基金：

美国国家科学基金会;

关键词：

metathesis; palladium; nucleosides; allylic alkylation;

D O I：

10.1016/j.tet.2004.07.009

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiomeric synthesis of L-cyclopentenyl nucleosides is described. The key intermediate (+)-cyclopentenyl alcohol (8) was prepared from methyl-alpha-D-galactopyranoside 1 using a ring closing metathesis reaction. Transformation of the allylic alcohol 8 into the allylic acetate (9) or carbonate (10), allows their coupling with purine and pyrimidine bases under Pd(0)-catalyzed Tsuji-Trost allylic alkylation's to yield 12a-c. The Pd catalyzed reaction was found to require the use of AlEt3. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：8397 / 8404

页数：8

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