Configuration and enantioselective synthesis of the fungus metabolite WF 14861

被引:5
作者
Detterbeck, R [1 ]
Hesse, M [1 ]
机构
[1] Univ Zurich, Inst Organ Chem, CH-8057 Zurich, Switzerland
关键词
D O I
10.1002/hlca.200390015
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A short enantioselective synthesis of the cathepsine inhibitor WF14861 (1) from the funghi Colletotrichum sp. as well as of its diasteroisomer 21 is presented. Comparison of the NMR data of the final products and, in particular, of the [alpha](D) values of the intermediates allowed the confirmation of the formerly proposed structure 1. In addition, the so far unknown absolute configuration of all three stereogenic centres of WF14861 could be established by this synthesis.
引用
收藏
页码:222 / 232
页数:11
相关论文
共 7 条
[1]  
Detterbeck R, 2002, HELV CHIM ACTA, V85, P1742, DOI 10.1002/1522-2675(200206)85:6<1742::AID-HLCA1742>3.0.CO
[2]  
2-E
[3]   Synthesis of tenuilobine, a bis-polyamine alkaloid from Oncinotis tenuiloba, and its transamidation to isotenuilobine [J].
Doll, MKH ;
Guggisberg, A ;
Hesse, M .
HELVETICA CHIMICA ACTA, 1996, 79 (02) :541-547
[4]   The synthesis of p-Cumaroylspermidines [J].
Hu, WQ ;
Hesse, M .
HELVETICA CHIMICA ACTA, 1996, 79 (02) :548-559
[5]   WF14861, a new cathepsins B and L inhibitor produced by Colletotrichum sp -: II.: Biological properties [J].
Otsuka, T ;
Muramatsu, Y ;
Niikura, K ;
Okamoto, M ;
Hino, M ;
Hashimoto, S .
JOURNAL OF ANTIBIOTICS, 1999, 52 (06) :542-547
[6]   REACTIONS OF HYDROGEN PEROXIDE .4. SODIUM TUNGSTATE CATALYZED EPOXIDATION OF ALPHA,BETA-UNSATURATED ACIDS [J].
PAYNE, GB ;
WILLIAMS, PH .
JOURNAL OF ORGANIC CHEMISTRY, 1959, 24 (01) :54-55
[7]  
TAMAI M, 1987, CHEM PHARM BULL, V35, P1098