Total synthesis of glycomaurrol and eustifoline-C by DIBAL-H promoted reductive ring opening of pyrano[2,3-c]carbazoles

被引：27

作者：

Hesse, Ronny ^{[1
]}

Schmidt, Arndt W. ^{[1
]}

Knoelker, Hans-Joachim ^{[1
]}

机构：

[1] Tech Univ Dresden, Dept Chem, D-01069 Dresden, Germany

来源：

TETRAHEDRON | 2015年 / 71卷 / 21期

关键词：

Carbazole; Pyranocarbazole; DIBAL-H; Reduction; Ring opening; 1ST TOTAL-SYNTHESIS; TRANSITION-METAL-COMPLEXES; ENANTIOSELECTIVE TOTAL-SYNTHESIS; CARBAZOLE ALKALOIDS; ORGANIC-SYNTHESIS; BOND FORMATION; ARYL HALIDES; CLAUSINE-L; A-D; CARQUINOSTATIN;

D O I：

10.1016/j.tet.2015.03.064

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed construction of the carbazole framework provides an efficient access to 3-hydroxy-6-methylcarbazole (glycozolinine) (5). Regioselective annulation of a pyran ring at glycozolinine (5) using either a C-5- or a C-10-building block leads to the pyrano[2,3-c]carbazole alkaloids glycomaurin (5,6-pyranoglycozoline, eustifoline-A) (2) and eustifoline-B (4), respectively. Reductive opening of the pyran ring with DIBAL-H in the presence of an additional Lewis acid transformed 2 into the 5-prenyl-substituted carbazole alkaloid glycomaurrol (1) and 4 into the 5-geranyl-substituted homologue eustifoline-C (3). (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：3485 / 3490

页数：6

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