Studies towards the synthesis of guanidine alkaloids; Synthesis of a tricyclic guanidine from succinimide

被引：32

作者：

Louwrier, S ^{[1
]}

Ostendorf, M ^{[1
]}

Tuynman, A ^{[1
]}

Hiemstra, H ^{[1
]}

机构：

[1] UNIV AMSTERDAM, AMSTERDAM INST MOLEC STUDIES, ORGAN CHEM LAB, 1018 WS AMSTERDAM, NETHERLANDS

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 06期

关键词：

D O I：

10.1016/0040-4039(95)02258-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a tricyclic guanidine as a model compound for ptilomycalin A and related guanidine alkaloids is described. The synthesis starts from succinimide and features an N-acyliminium ion coupling, an Eschenmoser sulfide-contraction and an N-guanylation as the key steps.

引用

页码：905 / 908

页数：4

共 30 条

[1] SYNTHESIS OF THE CARBAPENAM SYSTEM FROM GLUTAMIC-ACID AND ACETOACETIC ACID-DERIVATIVES
BACHI, MD
BREIMAN, R
MESHULAM, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (09) : 1439 - 1444
[2] CHEMOSELECTIVE AND DIASTEREOSELECTIVE REDUCTION OF BETA-ENAMINO ESTERS - A CONVENIENT SYNTHESIS OF BOTH CIS-GAMMA-AMINO AND TRANS-GAMMA-AMINO ALCOHOLS AND BETA-AMINO ESTERS
BARTOLI, G
CIMARELLI, C
MARCANTONI, E
PALMIERI, G
PETRINI, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) : 5328 - 5335
[3] CRAMBINE-C1 AND CRAMBINE-C2 - 2 FURTHER ICHTHYOTOXIC GUANIDINE ALKALOIDS FROM THE SPONGE CRAMBE-CRAMBE
BERLINCK, RGS
BRAEKMAN, JC
DALOZE, D
BRUNO, I
RICCIO, R
ROGEAU, D
AMADE, P
[J]. JOURNAL OF NATURAL PRODUCTS, 1992, 55 (04): : 528 - 532
[4] POLYCYCLIC GUANIDINE ALKALOIDS FROM THE MARINE SPONGE CRAMBE-CRAMBE AND CA++ CHANNEL BLOCKER ACTIVITY OF CRAMBESCIDIN-816
BERLINCK, RGS
BRAEKMAN, JC
DALOZE, D
BRUNO, I
RICCIO, R
FERRI, S
SPAMPINATO, S
SPERONI, E
[J]. JOURNAL OF NATURAL PRODUCTS, 1993, 56 (07): : 1007 - 1015
[5] 2 NEW GUANIDINE ALKALOIDS FROM THE MEDITERRANEAN SPONGE CRAMBE-CRAMBE
BERLINCK, RGS
BRAEKMAN, JC
DALOZE, D
HALLENGA, K
OTTINGER, R
BRUNO, I
RICCIO, R
[J]. TETRAHEDRON LETTERS, 1990, 31 (45) : 6531 - 6534
[6] ON THE ABSOLUTE-CONFIGURATION OF GEPHYROTOXIN
FUJIMOTO, R
KISHI, Y
[J]. TETRAHEDRON LETTERS, 1981, 22 (42) : 4197 - 4198
[7] THE APPLICATION OF THE SULFIDE CONTRACTION TO THE SYNTHESIS OF SOME SIMPLE PYRROLIDINE ALKALOIDS
GHIRLANDO, R
HOWARD, AS
KATZ, RB
MICHAEL, JP
[J]. TETRAHEDRON, 1984, 40 (15) : 2879 - 2884
[8] SODIUM-BOROHYDRIDE IN CARBOXYLIC-ACID MEDIA - A REVIEW OF THE SYNTHETIC UTILITY OF ACYLOXYBOROHYDRIDES
GRIBBLE, GW
NUTAITIS, CF
[J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1985, 17 (4-5) : 317 - 384
[9] GRILLOT AL, 1994, HETEROCYCLES, V39, P435
[10] SOME OBSERVATIONS REGARDING THE STEREOCHEMICAL COURSE OF IMINIUM ION REDUCTIONS - AN EXAMPLE OF THE SIZE DIFFERENCE BETWEEN SODIUM CYANOBOROHYDRIDE AND SODIUM TRIACETOXYBOROHYDRIDE
HART, DJ
LEROY, V
[J]. TETRAHEDRON, 1995, 51 (20) : 5757 - 5770

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