Total Syntheses of Murrayamine E, I, and K

被引：63

作者：

Schuster, Christian ^{[1
]}

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

Schnitzler, Heinrich ^{[1
]}

Hesse, Ronny ^{[1
]}

Jaeger, Anne ^{[1
]}

Schmidt, Arndt W. ^{[1
]}

Knoelker, Hans-Joachim ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 80卷 / 11期

关键词：

CARBAZOLE ALKALOIDS; BIOLOGICAL-ACTIVITY; RING-CLOSURE; KOENIGII; ETHERS; CONSTITUENTS; LEAVES;

D O I：

10.1021/acs.joc.5b00630

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe efficient synthetic routes to murrayamine A (mukoenine C), O-methylmurrayamine A, mahanine, O-methylmahanine, and murrayamine D and the first total syntheses of murrayamine E, I, and R.. Key steps are a palladium-catalyzed construction of the carbazole framework and an: annulation of the pyran ring, which is either catalyzed by phenylboronic acid or promoted by a Lewis acid.

引用

页码：5666 / 5673

页数：8

共 55 条

[1] CATALYTIC OXIDATIVE AROMATIC CYCLIZATIONS WITH PALLADIUM
AKERMARK, B
OSLOB, JD
HEUSCHERT, U
[J]. TETRAHEDRON LETTERS, 1995, 36 (08) : 1325 - 1326
[2] [Anonymous], 2002, SADABS V 2 10 BRUKER
[3] [Anonymous], 2002, PROG CH ORG NAT PROD
[4] ANWER F, 1972, Experientia (Basel), V28, P769, DOI 10.1007/BF01923117
[5] 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
BANDARANAYAKE, WM
BEGLEY, MJ
BROWN, BO
CLARKE, DG
CROMBIE, L
WHITING, DA
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (09): : 998 - 1007
[6] Synthesis of Pyrrole and Carbazole Alkaloids
Bauer, Ingmar
Knoelker, Hans-Joachim
[J]. ALKALOID SYNTHESIS, 2012, 309 : 203 - 253
[7] Bazouin A. R. M., 1964, French Patent, Patent No. 1436568
[8] BHATTACHARYYA P, 1985, INDIAN J CHEM B, V24, P452
[9] BHATTACHARYYA P, 1986, CHEM IND-LONDON, P246
[10] 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
BISSADA, S
LAU, CK
BERNSTEIN, MA
DUFRESNE, C
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (08): : 1866 - 1869

← 1 2 3 4 5 6 →