Total synthesis of anachelin H

被引:40
作者
Gademann, K [1 ]
Bethuel, Y [1 ]
机构
[1] Swiss Fed Inst Technol, Organ Chem Lab, CH-8093 Zurich, Switzerland
关键词
D O I
10.1021/ol048068x
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of anachelin H is reported. Starting from L-Ser, a stereodivergent synthesis of the polyketide fragment resulting in all possible diastereoisomers is described. The alkaloid peptide fragment is prepared via a tellurium-mediated oxidative aza annulation as the key step. Coupling of the fragments gave synthetic anachelin H, which was found to be identical to a sample of the natural product, thus confirming the configuration by total synthesis.
引用
收藏
页码:4707 / 4710
页数:4
相关论文
共 21 条
[1]  
Beiderbeck H, 2000, Z NATURFORSCH C, V55, P681
[2]   1,3-SYN DIASTEREOSELECTIVE REDUCTION OF BETA-HYDROXYKETONES UTILIZING ALKOXYDIALKYLBORANES [J].
CHEN, KM ;
HARDTMANN, GE ;
PRASAD, K ;
REPIC, O ;
SHAPIRO, MJ .
TETRAHEDRON LETTERS, 1987, 28 (02) :155-158
[3]   Oxidative cyclisation of N,N-dialkylcatechol amines to heterocyclic betaines via o-quinones:: synthetic, pulse radiolytic and enzyme studies [J].
Clews, J ;
Cooksey, CJ ;
Garratt, PJ ;
Land, EJ ;
Ramsden, CA ;
Riley, PA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (24) :4306-4315
[4]  
Drechsel H, 1998, J PEPT SCI, V4, P147, DOI 10.1002/(SICI)1099-1387(199805)4:3<147::AID-PSC136>3.3.CO
[5]  
2-3
[6]   DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE [J].
EVANS, DA ;
CHAPMAN, KT ;
CARREIRA, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (11) :3560-3578
[7]   A biomimetic route to the peptide alkaloid anachelin [J].
Gademann, K ;
Bethuel, Y .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (25) :3327-3329
[8]   The peptide alkaloid anachelin:: NMR spectroscopic evidence for β-turn formation in aqueous solution [J].
Gademann, K ;
Budzikiewicz, H .
CHIMIA, 2004, 58 (04) :212-214
[9]  
GADEMANN K, 2004, ANGEW CHEM, V116, P3389
[10]   The absolute stereochemistry of anachelins, siderophores from the cyanobacterium Anabaena cylindrica [J].
Ito, Y ;
Ishida, K ;
Okada, S ;
Murakami, M .
TETRAHEDRON, 2004, 60 (41) :9075-9080