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：

美国国家卫生研究院; 美国国家科学基金会;

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
OHTANI, I
MOORE, RE
RUNNEGAR, MTC
[J]. 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
PODLECH, J
SEEBACH, D
[J]. LIEBIGS ANNALEN, 1995, (07): : 1217 - 1228
[14] INHIBITION OF REDUCED GLUTATHIONE SYNTHESIS BY CYANOBACTERIAL ALKALOID CYLINDROSPERMOPSIN IN CULTURED RAT HEPATOCYTES
RUNNEGAR, MT
KONG, SM
ZHONG, YZ
LU, SC
[J]. 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
RUNNEGAR, MT
KONG, SM
ZHONG, YZ
GE, JL
LU, SC
[J]. 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
SEEBACH, D
WASMUTH, D
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (11): : 971 - 971
[17] SYNTHESIS OF A BICYCLIC MODEL FOR THE MARINE HEPATOTOXIN CYLINDROSPERMOPSIN
SNIDER, BB
HARVEY, TC
[J]. 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.
Snider, BB
Xie, CY
[J]. TETRAHEDRON LETTERS, 1998, 39 (39) : 7021 - 7024
[19] A convenient synthesis of di-guanidines (benzyloxycarbonyl)-protected guanidines
Su, WG
[J]. 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
TERAO, K
OHMORI, S
IGARASHI, K
OHTANI, I
WATANABE, MF
HARADA, KI
ITO, E
WATANABE, M
[J]. TOXICON, 1994, 32 (07) : 833 - 843

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