Total Synthesis of 7-and 8-Oxygenated Pyrano[3,2-a]carbazole and Pyrano[2,3-a]carbazole Alkaloids via Boronic Acid-Catalyzed Annulation of the Pyran Ring

被引：55

作者：

Julich-Gruner, Konstanze K. ^{[1
]}

Kataeva, Olga ^{[1
]}

Schmidt, Arndt W. ^{[1
]}

Knoelker, Hans-Joachim ^{[1
]}

机构：

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

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2014年 / 20卷 / 28期

关键词：

alkaloids; C-H bond activation; natural products; palladium; stereoselective catalysis; ACTIVE CARBAZOLE ALKALOIDS; CLAUSENA EXCAVATA. ISOLATION; TRANSITION-METAL-COMPLEXES; MURRAYA-KOENIGII; STRUCTURAL ELUCIDATION; ORGANIC-SYNTHESIS; MAHANINE; CONSTITUENTS; APOPTOSIS; CLOSURE;

D O I：

10.1002/chem.201403143

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The boronic acid-catalyzed annulation of citral opens up a short route to oxygenated cyclized monoterpenoid pyranocarbazole alkaloids. Thus, murrayamine-D is available in only three steps and 55% overall yield from the corresponding carbazole precursor.

引用

页码：8536 / 8540

页数：5

共 62 条

[1]

[Anonymous], SYNTHESIS

[2]

ANWER F, 1972, Experientia (Basel), V28, P769, DOI 10.1007/BF01923117

[3] SYNTHESES OF ACRIDONE AND CARBAZOLE ALKALOIDS INVOLVING PYRIDINE-CATALYZED CHROMEN FORMATION - CRYSTAL AND MOLECULAR-STRUCTURE OF DIBROMOCANNIBICYCLOL AND ITS BEARING ON STRUCTURES OF CYCLOL ALKALOIDS [J].

BANDARANAYAKE, WM ;

BEGLEY, MJ ;

BROWN, BO ;

CLARKE, DG ;

CROMBIE, L ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (09) :998-1007

[4] Synthesis of Pyrrole and Carbazole Alkaloids [J].

Bauer, Ingmar ;

Knoelker, Hans-Joachim .

ALKALOID SYNTHESIS, 2012, 309 :203-253

[5] HEPTAZOLICINE, A CARBAZOLE ALKALOID FROM CLAUSENA-HEPTAPHYLLA [J].

BHATTACHARYYA, P ;

CHAKRABORTY, A ;

CHOWDHURY, BK .

PHYTOCHEMISTRY, 1984, 23 (10) :2409-2410

[6] ONE-POT SYNTHESIS OF PRECOCENE-I AND PRECOCENE-II AND A FORMAL SYNTHESIS OF ROBUSTADIAL-A AND ROBUSTADIAL-B VIA 2-PHENYL-4H-1,3,2-BENZODIOXABORIN [J].

BISSADA, S ;

LAU, CK ;

BERNSTEIN, MA ;

DUFRESNE, C .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (08) :1866-1869

[7] STUDIES OF CHROMENES .10. OXIRANES OF NITROCHROMENES [J].

BROWN, PE ;

LEWIS, RA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (05) :573-577

[8]

Chakraborty D P, 1991, Fortschr Chem Org Naturst, V57, P71

[9]

Chakraborty D.P., 1993, ALKALOIDS, V44, P257

[10]

CHAKRABORTY DP, 1985, J INDIAN CHEM SOC, V62, P600

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