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The Azomethine Imine Route to Guanidines. Total Synthesis of (+)-Saxitoxin

Michael J. Martinelli ; Hall-Atwater Laboratories, Wesleyan University, Middletown ,Connecticut, USA 06457
Allen D. Brownstein ; Hall-Atwater Laboratories, Wesleyan University, Middletown ,Connecticut, USA 06457
Peter A. Jacobi ; Hall-Atwater Laboratories, Wesleyan University, Middletown ,Connecticut, USA 06457
Slovenka Polanc ; Department of Chemistry, E. Kardelj University 61000 Ljubljana, Jugoslavija

Puni tekst: engleski, pdf (11 MB) str. 267-295 preuzimanja: 160* citiraj
APA 6th Edition
Martinelli, M.J., Brownstein, A.D., Jacobi, P.A. i Polanc, S. (1986). The Azomethine Imine Route to Guanidines. Total Synthesis of (+)-Saxitoxin. Croatica Chemica Acta, 59 (1), 267-295. Preuzeto s https://hrcak.srce.hr/177593
MLA 8th Edition
Martinelli, Michael J., et al. "The Azomethine Imine Route to Guanidines. Total Synthesis of (+)-Saxitoxin." Croatica Chemica Acta, vol. 59, br. 1, 1986, str. 267-295. https://hrcak.srce.hr/177593. Citirano 21.06.2021.
Chicago 17th Edition
Martinelli, Michael J., Allen D. Brownstein, Peter A. Jacobi i Slovenka Polanc. "The Azomethine Imine Route to Guanidines. Total Synthesis of (+)-Saxitoxin." Croatica Chemica Acta 59, br. 1 (1986): 267-295. https://hrcak.srce.hr/177593
Harvard
Martinelli, M.J., et al. (1986). 'The Azomethine Imine Route to Guanidines. Total Synthesis of (+)-Saxitoxin', Croatica Chemica Acta, 59(1), str. 267-295. Preuzeto s: https://hrcak.srce.hr/177593 (Datum pristupa: 21.06.2021.)
Vancouver
Martinelli MJ, Brownstein AD, Jacobi PA, Polanc S. The Azomethine Imine Route to Guanidines. Total Synthesis of (+)-Saxitoxin. Croatica Chemica Acta [Internet]. 1986 [pristupljeno 21.06.2021.];59(1):267-295. Dostupno na: https://hrcak.srce.hr/177593
IEEE
M.J. Martinelli, A.D. Brownstein, P.A. Jacobi i S. Polanc, "The Azomethine Imine Route to Guanidines. Total Synthesis of (+)-Saxitoxin", Croatica Chemica Acta, vol.59, br. 1, str. 267-295, 1986. [Online]. Dostupno na: https://hrcak.srce.hr/177593. [Citirano: 21.06.2021.]

Sažetak
Azomethine imines may be readily generated through the
interaction of aldehyde aeetals with earboxylie acid hydrazides.
These reaetions are most highly favored in pollar aprotie solvents
and aeid eatalysis is required. With suitably funetionalized
hydrazides these substanees undergo a faeile intramolecular addition
to give fused-ring pyrazolidine derivati ves. As a part of these
studies, (± )-Saxitoxin (7), the paralytie agent of the Alaska butter
elam Saxidomas giganteus, has been synthesized in a totally stereospecific fashion through a sequenee involving as the key steps:
(a) intramolecular 1,3-dipolar addition of an azomethine imine to
a 2-imidazolone; (b) reductive cleavage of the resulting pyrazolidine
ring followed by intramoleeular acylation; and (c) final elaboration of a bis-pseudourea to the requisite guanidine functionality.

Hrčak ID: 177593

URI
https://hrcak.srce.hr/177593

Posjeta: 273 *