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

[1] Identification of cylindrospermopsin in Aphanizomenon ovalisporum (Cyanophyceae) isolated from Lake Kinneret, Israel
Banker, R
Carmeli, S
Hadas, O
Teltsch, B
Porat, R
Sukenik, A
[J]. JOURNAL OF PHYCOLOGY, 1997, 33 (04) : 613 - 616
[2] ASYMMETRIC CARBON CARBON BOND FORMATION VIA BETA-ALLYLDIISOPINOCAMPHEYLBORANE - SIMPLE SYNTHESIS OF SECONDARY HOMOALLYLIC ALCOHOLS WITH EXCELLENT ENANTIOMERIC PURITIES
BROWN, HC
JADHAV, PK
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) : 2092 - 2093
[3] READILY ACCESSIBLE 12-I-5 OXIDANT FOR THE CONVERSION OF PRIMARY AND SECONDARY ALCOHOLS TO ALDEHYDES AND KETONES
DESS, DB
MARTIN, JC
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) : 4155 - 4156
[4] CONVERSION OF ALCOHOLS TO PROTECTED GUANIDINES USING THE MITSUNOBU PROTOCOL
DODD, DS
KOZIKOWSKI, AP
[J]. TETRAHEDRON LETTERS, 1994, 35 (07) : 977 - 980
[5] DU X, 1997, THESIS U CALIFORNIA
[6] DIASTEREOSELECTIVE ALKYLATION OF 3-AMINOBUTANOIC ACID IN THE 2-POSITION
ESTERMANN, H
SEEBACH, D
[J]. HELVETICA CHIMICA ACTA, 1988, 71 (07) : 1824 - 1839
[7] ISOLATION OF CYLINDROSPERMOPSIN FROM A CYANOBACTERIUM UMEZAKIA NATANS AND ITS SCREENING METHOD
HARADA, K
OHTANI, I
IWAMOTO, K
SUZUKI, M
WATANABE, MF
WATANABE, M
TERAO, K
[J]. TOXICON, 1994, 32 (01) : 73 - 84
[8] Isolation and toxicity of Cylindrospermopsis raciborskii from an ornamental lake
Hawkins, PR
Chandrasena, NR
Jones, GJ
Humpage, AR
Falconer, IR
[J]. TOXICON, 1997, 35 (03) : 341 - 346
[9] Imino Diels-Alder-based construction of a piperidine A-ring unit for total synthesis of the marine hepatotoxin cylindrospermopsin
Heintzelman, GR
Weinreb, SM
Parvez, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) : 4594 - 4599
[10] HEINTZELMAN GR, 1993, SYNLETT, P551

← 1 2 →