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 55 条

[1] The reactivity of the N-Boc protecting group:: an underrated feature
Agami, C
Couty, F
[J]. TETRAHEDRON, 2002, 58 (14) : 2701 - 2724
[2] Alcaide B, 2002, EUR J ORG CHEM, V2002, P1595
[3] Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam
Amat, M
Llor, N
Hidalgo, J
Escolano, C
Bosch, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) : 1919 - 1928
[4] Armas PD, 1998, TETRAHEDRON LETT, V39, P131
[5] Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application
Asano, N
Nash, RJ
Molyneux, RJ
Fleet, GWJ
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (08) : 1645 - 1680
[6] Synthesis of (+)-8-deoxyvernolepin and its 11,13-dihydroderivative.: A novel reaction initiated by sulfene elimination leads to the 2-oxa-cis-decalin skeleton
Barrero, AF
Oltra, JE
Alvarez, M
Rosales, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) : 5461 - 5469
[7] A new strategy for the synthesis of (+)-vernolepin related compounds:: an unusual sulfene elimination leads to the 2-oxa-cis-decalin skeleton
Barrero, AF
Oltra, JE
Alvarez, M
[J]. TETRAHEDRON LETTERS, 2000, 41 (40) : 7639 - 7643
[8] Beck G, 2002, SYNLETT, P837
[9] BECK G, 1990, COMPREHENSIVE MED CH, V3
[10] BECK G, 1990, COMPREHENSIVE MED CH, V2

← 1 2 3 4 5 6 →