Stereoselective synthesis of a tricyclic guanidinium model of cylindrospermopsin

被引：43

作者：

McAlpine, IJ ^{[1
]}

Armstrong, RW ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 12期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

cylindrospermopsin; guanidines; piperidines;

D O I：

10.1016/S0040-4039(99)02348-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An 11-step enantioselective synthesis of the A-ring of cylindrospermopsin is described using an intramolecular conjugate addition as the key step to forming the piperidine ring. Further elaboration generates a tricyclic guanidine via a sequential double displacement strategy as a model for the cylindrospermopsin guanidinium core. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1849 / 1853

页数：5

共 20 条

[11]

MOORE RE, 1993, GAZZ CHIM ITAL, V123, P329

[12] CYLINDROSPERMOPSIN - A POTENT HEPATOTOXIN FROM THE BLUE-GREEN-ALGA CYLINDROSPERMOPSIS-RACIBORSKII [J].

OHTANI, I ;

MOORE, RE ;

RUNNEGAR, MTC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (20) :7941-7942

[13] ON THE PREPARATION OF BETA-AMINO ACIDS FROM ALPHA-AMINO-ACIDS USING THE ARNDT-EISTERT REACTION - SCOPE, LIMITATIONS AND STEREOSELECTIVITY. APPLICATION TO CARBOHYDRATE PEPTIDATION - STEREOSELECTIVE ALPHA-ALKYLATIONS OF SOME BETA-AMINO ACIDS [J].

PODLECH, J ;

SEEBACH, D .

LIEBIGS ANNALEN, 1995, (07) :1217-1228

[14] INHIBITION OF REDUCED GLUTATHIONE SYNTHESIS BY CYANOBACTERIAL ALKALOID CYLINDROSPERMOPSIN IN CULTURED RAT HEPATOCYTES [J].

RUNNEGAR, MT ;

KONG, SM ;

ZHONG, YZ ;

LU, SC .

BIOCHEMICAL PHARMACOLOGY, 1995, 49 (02) :219-225

[15] THE ROLE OF GLUTATHIONE IN THE TOXICITY OF A NOVEL CYANOBACTERIAL ALKALOID CYLINDROSPERMOPSIN IN CULTURED RAT HEPATOCYTES [J].

RUNNEGAR, MT ;

KONG, SM ;

ZHONG, YZ ;

GE, JL ;

LU, SC .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1994, 201 (01) :235-241

[16] ALKYLATION OF AMINO-ACIDS WITHOUT LOSS OF OPTICAL-ACTIVITY - ALPHA-ALKYLATION AND BETA-ALKYLATION OF AN ASPARTIC-ACID DERIVATIVE [J].

SEEBACH, D ;

WASMUTH, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (11) :971-971

[17] SYNTHESIS OF A BICYCLIC MODEL FOR THE MARINE HEPATOTOXIN CYLINDROSPERMOPSIN [J].

SNIDER, BB ;

HARVEY, TC .

TETRAHEDRON LETTERS, 1995, 36 (26) :4587-4590

[18] Model studies for the synthesis of the marine hepatotoxin cylindrospermopsin. Preparation of a bicyclic guanidine with the hydroxymethyluracil side chain. [J].

Snider, BB ;

Xie, CY .

TETRAHEDRON LETTERS, 1998, 39 (39) :7021-7024

[19] A convenient synthesis of di-guanidines (benzyloxycarbonyl)-protected guanidines [J].

Su, WG .

SYNTHETIC COMMUNICATIONS, 1996, 26 (02) :407-413

[20] ELECTRON-MICROSCOPIC STUDIES ON EXPERIMENTAL POISONING IN MICE INDUCED BY CYLINDROSPERMOPSIN ISOLATED FROM BLUE-GREEN-ALGA UMEZAKIA NATANS [J].

TERAO, K ;

OHMORI, S ;

IGARASHI, K ;

OHTANI, I ;

WATANABE, MF ;

HARADA, KI ;

ITO, E ;

WATANABE, M .

TOXICON, 1994, 32 (07) :833-843

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