Synthesis of optically pure Clausenamine-A and its demethoxylated analogs

被引：62

作者：

Lin, GQ ^{[1
]}

Zhang, AM ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

TETRAHEDRON | 2000年 / 56卷 / 37期

基金：

中国国家自然科学基金;

关键词：

Plasmodium falciparum; clausemine-A; Suzuki cross-coupling reaction; resolution;

D O I：

10.1016/S0040-4020(00)00634-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of Clansenamine-A (3) was developed involving the Suzuki cross-coupling and oxidative coupling reaction. The synthesis of its demethoxylated analogs 1 and 2 were also reported. Resolution of(+)-1, (+)-2, (+)-3 and (-)-1, (-)-2, (-)-3 were performed via their corresponding camphorsulfonates of the racemates. The absolute configurations of(+)-1, (+)-2, (+)-3 and (-)-1, (-)-2, (-)-3 were assigned as (aR) and (aS), respectively, by X-ray analysis and their CD spectrum. The primarily cytotoxic activities of these biscarbazoles against Plasmodium falciparum were briefly described. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7163 / 7171

页数：9

共 33 条

[21] Electrophilic aromatic bromination using bromodimethylsulfonium bromide generated in situ [J].

Majetich, G ;

Hicks, R ;

Reister, S .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) :4321-4326

[22] Palladium-catalyzed amination of aryl bromides: Use of phosphinoether ligands for the efficient coupling of acyclic secondary amines [J].

Marcoux, JF ;

Wagaw, S ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06) :1568-1569

[23] STOICHIOMETRIC SYNTHESIS OF UNSYMMETRICAL MONONITROBIPHENYLS VIA THE PALLADIUM-CATALYZED CROSS-COUPLING OF ARYLBORONIC ACIDS WITH ARYL BROMIDES [J].

MILLER, RB ;

DUGAR, S .

ORGANOMETALLICS, 1984, 3 (08) :1261-1263

[24] A REGIOSPECIFIC TOTAL SYNTHESIS OF ELLIPTICINE VIA NITRENE INSERTION [J].

MILLER, RB ;

DUGAR, S .

TETRAHEDRON LETTERS, 1989, 30 (03) :297-300

[25] Fischer indolization of 2-sulfonyloxyphenylhydrazones: A new and practical approach for preparing 7-oxygenated indoles and application to the first synthesis of eudistomidin-A (Fischer indolization and its related compounds, Part 28) [J].

Murakami, Y ;

Watanabe, T ;

Takahashi, H ;

Yokoo, H ;

Nakazawa, Y ;

Koshimizu, H ;

Adachi, N ;

Kurita, M ;

Yoshino, T ;

Inagaki, T ;

Ohishi, M ;

Watanabe, M ;

Tani, M ;

Yokoyama, Y .

TETRAHEDRON, 1998, 54 (1-2) :45-64

[26] Synthesis and chiroptical properties of axially chiral, binaphthol-based oligomers [J].

Ng, MK ;

Chow, HF ;

Chan, TL ;

Mak, TCW .

TETRAHEDRON LETTERS, 1996, 37 (17) :2979-2982

[27] SYNTHESIS OF THE ACRIDONE ALKALOIDS GLYFOLINE AND CONGENERS - STRUCTURE ACTIVITY RELATIONSHIP STUDIES OF CYTOTOXIC ACRIDONES [J].

SU, TL ;

KOHLER, B ;

CHOU, TC ;

CHUN, MW ;

WATANABE, KA .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (14) :2703-2710

[28] Room temperature catalytic amination of aryl iodides [J].

Wolfe, JP ;

Buchwald, SL .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :6066-6068

[29]

WOOD JL, 1997, J AM CHEM SOC, V119, P9647

[30] Carbazole-pyranocoumarin dimer and binary carbazole alkaloid from Clausena excavata [J].

Wu, TS ;

Huang, SC ;

Wu, PL .

TETRAHEDRON LETTERS, 1996, 37 (43) :7819-7822

← 1 2 3 4 →