Construction of a chiral quaternary carbon center by a radical cyclization/ring-enlargement reaction: synthesis of 4α-azidoethyl carbocyclic ribose, a key unit for the synthesis of cyclic ADP-ribose derivatives of biological importance

被引：5

作者：

Sato, Takatoshi ^{[1
]}

Tsuzuki, Takayoshi ^{[1
]}

Takano, Satoshi ^{[1
]}

Kato, Kohtaro ^{[1
]}

Fukuda, Hayato ^{[1
]}

Arisawa, Mitsuhiro ^{[1
]}

Shuto, Satoshi ^{[1
,2
]}

机构：

[1] Hokkaido Univ, Fac Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan

[2] Hokkaido Univ, Ctr Res & Educ Drug Discovery, Kita Ku, Sapporo, Hokkaido 0600812, Japan

来源：

TETRAHEDRON | 2015年 / 71卷 / 33期

关键词：

Cyclic ADP-ribose; Radical reaction; Silicon tether; Quaternary carbon center; Carbocyclic ribose; Ring-enlargement; (3-OXA-2-SILACYCLOPENTYL)METHYL RADICALS; CA2+-MOBILIZING 2ND-MESSENGER; STEREOSELECTIVE INTRODUCTION; ANALOGS; ANTAGONISTS; CHEMISTRY; RELEASE; LINKAGE; ENTRY;

D O I：

10.1016/j.tet.2015.05.084

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

As a stable analog of the second messenger cyclic ADP-ribose (cADPR), we designed 4 ''-azidoethyl-cyclic ADP-carbocylic-ribose (N-3-cADPcR). For the synthesis of N-3-cADPcR, 1 beta-amino-2,3-O-isoproplylidene-4 alpha-azidoethyl carbocyclic-ribose (4) having a chiral quaternary stereogenic center is required as the key unit. We successfully synthesized the desired unit 4 via construction of the quaternary stereogenic center by a radical cyclization/ring-enlargement reaction with a silicon-tethered substrate as the key step. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：5407 / 5413

页数：7

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