Total synthesis of the antimalarial naphthylisoquinoline alkaloid 5-epi-4′-O-demethylancistrobertsonine C by asymmetric Suzuki cross-coupling

被引：42

作者：

Bringmann, Gerhard ^{[1
]}

Ruedenauer, Stefan ^{[1
]}

Bruhn, Torsten ^{[1
]}

Benson, Lauren ^{[1
]}

Brun, Reto ^{[2
]}

机构：

[1] Univ Wurzburg, Inst Organ Chem, D-97074 Wurzburg, Germany

[2] Swiss Trop Inst, CH-4002 Basel, Switzerland

来源：

TETRAHEDRON | 2008年 / 64卷 / 23期

关键词：

naphthylisoquinoline alkaloids; Suzuki cross-coupling; absolute configuration; quantum chemical CD calculations; chiral ligands;

D O I：

10.1016/j.tet.2008.03.087

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of the antimalarial naphthylisoquinoline alkaloid 5-epi-4'-O-demethylancistrobertsonine C (1a) and its-as yet unnatural-atropo-diastereomer, 1b, is described. The key step of the synthesis is the construction of the rotationally hindered and thus stereogenic biaryl axis, which was built up by a Suzuki reaction. The use of chiral ligands in the palladium-catalyzed cross-coupling permitted to increase the low internal asymmetric induction up to a diastereomeric ratio of 74:26. The assignment of the axial configurations of the atropo-diastereomers was achieved by 2D NMR experiments and corroborated by quantum chemical CD calculations. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5563 / 5568

页数：6

共 53 条

[1] The asymmetric Suzuki coupling route to axially chiral biaryls [J].

Baudoin, O .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (20) :4223-4229

[2] A NEW MIXING OF HARTREE-FOCK AND LOCAL DENSITY-FUNCTIONAL THEORIES [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (02) :1372-1377

[3] ACETOGENIC ISOQUINOLINE ALKALOIDS .17. 1ST TOTAL SYNTHESIS OF (-)-DIONCOPHYLLINE-A (TRIPHYOPHYLLINE) AND OF SELECTED STEREOISOMERS - COMPLETE (REVISED) STEREOSTRUCTURE [J].

BRINGMANN, G ;

JANSEN, JR ;

REUSCHER, H ;

RUBENACKER, M ;

PETERS, K ;

VONSCHNERING, HG .

TETRAHEDRON LETTERS, 1990, 31 (05) :643-646

[4] Novel concepts in directed biaryl synthesis, part 102. The directed synthesis of axially chiral ligands, reagents, catalysts, and natural products through the 'lactone methodology' [J].

Bringmann, G ;

Tasler, S ;

Pfeifer, RM ;

Breuning, M .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 661 (1-2) :49-65

[5]

Bringmann G, 2001, PROG CH ORG NAT PROD, V82, P1

[6] Acetogenic isoquinoline alkaloids, part 147.: First total synthesis of the 7,6′-coupled antifungal naphthylisoquinoline alkaloid dioncophylline B [J].

Bringmann, G ;

Günther, C ;

Peters, EM ;

Peters, K .

TETRAHEDRON, 2001, 57 (07) :1253-1259

[7] Stress-related polyketide metabolism of dioncophyllaceae and ancistrocladaceae [J].

Bringmann, G ;

Feineis, D .

JOURNAL OF EXPERIMENTAL BOTANY, 2001, 52 (363) :2015-2022

[8] ACETOGENIC ISOQUINOLINE ALKALOIDS .20. ATROP-DIASTEREOMER SEPARATION BY RACEMATE RESOLUTION TECHNIQUES - N-METHYL-DIONCOPHYLLINE-A AND ITS 7-EPIMER FROM ANCISTROCLADUS-ABBREVIATUS [J].

BRINGMANN, G ;

LISCH, D ;

REUSCHER, H ;

ASSI, LA ;

GUNTHER, K .

PHYTOCHEMISTRY, 1991, 30 (04) :1307-1310

[9]

Bringmann G, 2000, ANGEW CHEM INT EDIT, V39, P1464, DOI 10.1002/(SICI)1521-3773(20000417)39:8<1464::AID-ANIE1464>3.0.CO

[10]

2-#

← 1 2 3 4 5 6 →