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

被引：41

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

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