Pictet-Spengler synthesis of tetrahydro-β-carbolines using vinylsulfonylmethyl resin

被引:19
作者
Connors, RV [1 ]
Zhang, AJ [1 ]
Shuttleworth, SJ [1 ]
机构
[1] Tularik Inc, San Francisco, CA 94080 USA
关键词
D O I
10.1016/S0040-4039(02)01341-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel, solid phase Pictet-Spengler synthesis has been developed using vinylsulfonylmethyl resin. A library of 800 structurally diverse tetrahydro-beta-carbolines was prepared in a four-step sequence starting from tryptamines. The final resin cleavage step enabled the introduction of a basic tertiary amine in the six-membered heterocyclic ring. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6661 / 6663
页数:3
相关论文
共 11 条
[1]   THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].
COX, ED ;
COOK, JM .
CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842
[2]   Solid phase sequential 1,3-dipolar cycloaddition-Pictet-Spengler reactions [J].
Dondas, HA ;
Grigg, R ;
MacLachlan, WS ;
MacPherson, DT ;
Markandu, J ;
Sridharan, V ;
Suganthan, S .
TETRAHEDRON LETTERS, 2000, 41 (06) :967-970
[3]   N-terminal peptide aldehydes as electrophiles in combinatorial solid phase synthesis of novel peptide isosteres [J].
Groth, T ;
Meldal, M .
JOURNAL OF COMBINATORIAL CHEMISTRY, 2001, 3 (01) :45-63
[4]  
KALIJUSTE K, 1995, TETRAHEDRON LETT, V36, P9211
[5]   Resin-immobilised benzyl and aryl vinyl sulfones: New versatile traceless linkers for solid-phase organic synthesis [J].
Kroll, FEK ;
Morphy, R ;
Rees, D ;
Gani, D .
TETRAHEDRON LETTERS, 1997, 38 (49) :8573-8576
[6]   Solid-phase synthesis of 1,2,3,4-tetrahydro-β-carboline-containing peptidomimetics [J].
Li, XF ;
Zhang, LS ;
Zhang, W ;
Hall, SE ;
Tam, JP .
ORGANIC LETTERS, 2000, 2 (20) :3075-3078
[7]   Application of the Pictet-Spengler reaction in combinatorial chemistry. [J].
Mayer, JP ;
BankaitisDavis, D ;
Zhang, JW ;
Beaton, G ;
Bjergarde, K ;
Andersen, CM ;
Goodman, BA ;
Herrera, CJ .
TETRAHEDRON LETTERS, 1996, 37 (32) :5633-5636
[8]   Pictet-Spengler reaction on solid support: Synthesis of 1,2,3,4-tetrahydro-beta-carboline libraries [J].
Mohan, R ;
Chou, YL ;
Morrissey, MM .
TETRAHEDRON LETTERS, 1996, 37 (23) :3963-3966
[9]   On the formation of isochinolin-derivatives through the development of methylial on phenyl-aether, phenyl-alanin and tyrosin. [J].
Pictet, A ;
Spengler, T .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1911, 44 :2030-2036
[10]   The N-acyliminium Pictet-Spengler condensation as a multicomponent combinatorial reaction on solid phase and its application to the synthesis of demethoxyfumitremorgin C analogues [J].
Wang, HS ;
Ganesan, A .
ORGANIC LETTERS, 1999, 1 (10) :1647-1649