Synthesis of alkaloid analogues from α-amino acids by one-pot radical decarboxylation/alkylation

被引：22
作者：
Boto, A [1 ]
De León, Y [1 ]
Gallardo, JA [1 ]
Hernández, R [1 ]
机构：
[1] CSIC, Inst Prod Nat & Agrobiol, San Cristobal la Laguna 38206, Spain
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 16期
关键词：
alkaloids; amino acids; nitrogen heterocycles; radical reactions; spiro compounds;
D O I：
10.1002/ejoc.200500124
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild, one-pot methodology to obtain a-substituted nitrogen heterocycles from commercial amino acids is reported. This versatile procedure has been applied to the synthesis of different alkaloid analogues in good to excellent yields. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
引用
收藏
页码：3461 / 3468
页数：8
相关论文
共 125 条
[1]   DESIGN, SYNTHESIS, AND TESTING OF POTENTIAL ANTISICKLING AGENTS .5. DISUBSTITUTED BENZOIC-ACIDS DESIGNED FOR THE DONOR SITE AND PROLINE SALICYLATES DESIGNED FOR THE ACCEPTOR SITE [J].
ABRAHAM, DJ ;
GAZZE, DM ;
KENNEDY, PE ;
MOKOTOFF, M .
JOURNAL OF MEDICINAL CHEMISTRY, 1984, 27 (12) :1549-1559
[2]   The reactivity of the N-Boc protecting group:: an underrated feature [J].
Agami, C ;
Couty, F .
TETRAHEDRON, 2002, 58 (14) :2701-2724
[3]   Useful dual Diels-Alder Behavior of 2-azetidinone-tethered aryl imines as azadienophiles or azadienes:: A β-lactam-based stereocontrolled access to optically pure highly functionalized indolizidine systems [J].
Alcaide, B ;
Almendros, P ;
Alonso, JM ;
Aly, MF .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (14) :3415-3426
[4]   Stereoselective synthesis of the indolizinoindole ring system [J].
Allin, SM ;
Thomas, CI ;
Allard, JE ;
Duncton, M ;
Elsegood, MRJ ;
Edgar, M .
TETRAHEDRON LETTERS, 2003, 44 (11) :2335-2337
[5]   Stereoselective synthesis of isoquinoline derivatives from bicyclic lactam templates [J].
Allin, SM ;
Vaidya, DG ;
James, SL ;
Allard, JE ;
Smith, TAD ;
McKee, V ;
Martin, WP .
TETRAHEDRON LETTERS, 2002, 43 (20) :3661-3663
[6]  
[Anonymous], [No title captured]
[7]  
Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO
[8]  
2-E
[9]   Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application [J].
Asano, N ;
Nash, RJ ;
Molyneux, RJ ;
Fleet, GWJ .
TETRAHEDRON-ASYMMETRY, 2000, 11 (08) :1645-1680
[10]   Spiro cyclisations of N-acyliminium ions involving an aromatic π-nucleophile [J].
Bailey, PD ;
Morgan, KM ;
Smith, DI ;
Vernon, JM .
TETRAHEDRON, 2003, 59 (18) :3369-3378
12345678910