Synthesis of alkaloids from aminol derivatives by β-fragmentation of primary alkoxyl radicals

被引：16

作者：

Boto, A ^{[1
]}

Hernández, R ^{[1
]}

Montoya, A ^{[1
]}

Suárez, E ^{[1
]}

机构：

[1] CSIC, Inst Prod Nat & Agrobiol, San Cristobal la Laguna 38206, Spain

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 07期

关键词：

radicals; alkaloids; acyliminium ions; fragmentation; nucleophilic addition; nitrogen heterocycles; synthesis;

D O I：

10.1016/j.tetlet.2003.12.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The fragmentation of primary alkoxyl radicals, often described as low yielding and plagued by side reactions, proceeded in good to excellent yields when aminol derivatives were used as substrates. Remarkably, no side reactions such as hydrogen abstraction or oxidation were observed. The fragmentation can be coupled with an alkylation reaction to give 2-substituted pyrrolidine and piperidine rings such as alkaloid analogues and functionalized, chiral nitrogen heterocycles. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：1559 / 1563

页数：5

共 50 条

[1] Synthesis of unnatural amino acids from serine derivatives by β-fragmentation of primary alkoxyl radicals
Bow, Alicia
Gallardo, Juan A.
Hernandez, Dacil
Hernandez, Rosendo
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (19): : 7260 - 7269
[2] Synthesis of alkaloid analogues from β-amino alcohols by β-fragmentation of primary alkoxyl radicals
Boto, Alicia
Hernandez, Dacil
Hernandez, Rosendo
Montoya, Adriana
Suarez, Ernesto
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (02) : 325 - 334
[3] Synthesis of α,ω-differently substituted cyclic ethers from carbohydrates by β-fragmentation of alkoxyl radicals
Boto, A
Hernández, R
Suárez, E
TETRAHEDRON LETTERS, 2002, 43 (10) : 1821 - 1824
[4] β-fragmentation of primary alkoxyl radicals versus hydrogen abstraction:: Synthesis of polyols and α,ω-differently substituted cyclic ethers from carbohydrates
Boto, A
Hernández, D
Hernández, R
Suárez, E
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (13): : 5310 - +
[5] β-fragmentation of alkoxyl radicals:: Natural bond orbital analysis
Leblanc, M
Siri, D
Marque, SRA
Grimaldi, S
Bertin, D
Tordo, P
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2006, 106 (03) : 676 - 685
[6] FORMATION AND FRAGMENTATION OF ALKOXYL RADICALS BY OXIDATION OF ALCOHOLS WITH PEROXYDISULFATE ION
LEDWITH, A
RUSSELL, PJ
SUTCLIFF.LH
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1973, (05): : 630 - 633
[7] Synthesis of Chiral β-lodo- and Vinylorganophosphorus(V) Compounds by Fragmentation of Carbohydrate Anomeric Alkoxyl Radicals
Hernandez-Guerra, Daniel
Rodriguez, Maria S.
Suarez, Ernesto
ORGANIC LETTERS, 2013, 15 (02) : 250 - 253
[8] Fragmentation of carbohydrate anomeric alkoxyl radicals.: Synthesis of highly functionalized chiral vinyl sulfones
Alonso-Cruz, CR
León, EI
Ortiz-López, FJ
Rodríguez, MS
Suárez, E
TETRAHEDRON LETTERS, 2005, 46 (32) : 5265 - 5268
[9] Fragmentation of Carbohydrate Anomeric Alkoxyl Radicals: Synthesis of Chiral Polyhydroxylated β-Iodo- and Alkenylorganophosphorus(V) Compounds
Hernandez-Guerra, Daniel
Rodriguez, Maria S.
Suarez, Ernesto
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (23) : 5033 - 5055
[10] Fragmentation of carbohydrate anomeric alkoxyl radicals:: A new synthesis of 1,1-difluoro-1-iodo alditols
Francisco, CG
González, CC
Paz, NR
Suárez, E
ORGANIC LETTERS, 2003, 5 (22) : 4171 - 4173

← 1 2 3 4 5 →