Synthesis and structure elucidation of open-chained putrescine-bisamides from Aglaia species

被引:21
作者
Detterbeck, R [1 ]
Hesse, M [1 ]
机构
[1] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland
关键词
putrescine-bisamides; Aglaia; hemileptagline; aglaidithioduline; aglaithioduline; grandiamide B and C; aglaiduline; pyramidatine; secopiriferine; secoodorine;
D O I
10.1016/S0040-4020(02)00751-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The structures of the eight recently described open-chained putrescine bisamide alkaloids secoodorine (1), aglaithioduline (3), aglaiduline (4), aglaidithioduline (5), grandiamide B (13), grandiamide C (14), pyramidatine (20), and secopiriferine (22), which were isolated from different Aglaia species, have been verified by synthesis. In addition to that, the published structure 2 for hemileptagline had to be revised, and for secoodorine (1) the absolute configuration could be established. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6887 / 6893
页数:7
相关论文
共 10 条
[1]   (2R)-5-ALKYL-2-TERT-BUTYL-6-METHYL-4H-1,3-DIOXIN-4-ONES AS INTERMEDIATES FOR THE PREPARATION OF ALPHA-BETA-BETA-TRISUBSTITUTED BETA-HYDROXYCARBOXYLIC ACIDS FROM (R)-3-HYDROXYBUTYRIC ACID UNDER SELF-REGENERATION OF THE STEREOGENIC CENTER [J].
AMBERG, W ;
SEEBACH, D .
CHEMISCHE BERICHTE, 1990, 123 (12) :2429-2438
[2]  
BIENZ S, 2002, PUTRESCINE SPERMIDIN
[3]   Insecticidal flavaglines and other compounds from Fijian Aglaia species [J].
Greger, H ;
Pacher, T ;
Brem, B ;
Bacher, M ;
Hofer, O .
PHYTOCHEMISTRY, 2001, 57 (01) :57-64
[4]   Infraspecific variation of sulfur-containing bisamides from Aglaia leptantha [J].
Greger, H ;
Pacher, T ;
Vajrodaya, S ;
Bacher, M ;
Hofer, O .
JOURNAL OF NATURAL PRODUCTS, 2000, 63 (05) :616-620
[5]  
IKEGAMI F, 1989, CHEM PHARM BULL, V37, P1932
[6]   Three putrescine bisamides from the leaves of Aglaia grandis [J].
Inada, A ;
Shono, K ;
Murata, H ;
Inatomi, Y ;
Darnaedi, D ;
Nakanishi, T .
PHYTOCHEMISTRY, 2000, 53 (08) :1091-1095
[7]   MONO-PROTECTED DIAMINES - N-TERT-BUTOXYCARBONYL-ALPHA,OMEGA-ALKANEDIAMINES FROM ALPHA,OMEGA-ALKANEDIAMINES [J].
KRAPCHO, AP ;
KUELL, CS .
SYNTHETIC COMMUNICATIONS, 1990, 20 (16) :2559-2564
[8]  
MEDEIROS EFD, 1991, J CHEM SOC P1, P2725
[9]   BISAMIDES FROM AGLAIA SPECIES - STRUCTURE-ANALYSIS AND POTENTIAL TO REVERSE DRUG-RESISTANCE WITH CULTURED-CELLS [J].
SAIFAH, E ;
PURIPATTANAVONG, J ;
LIKHITWITAYAWUID, K ;
CORDELL, GA ;
CHAI, H ;
PEZZUTO, JM .
JOURNAL OF NATURAL PRODUCTS, 1993, 56 (04) :473-477
[10]   Bisamides from Aglaia edulis [J].
Saifah, E ;
Suttisri, R ;
Shamsub, S ;
Pengsuparp, T ;
Lipipun, V .
PHYTOCHEMISTRY, 1999, 52 (06) :1085-1088