Total synthesis of 7-deoxypancratistatin-1-carboxaldehyde and carboxylic acid via solvent-free intramolecular aziridine opening: Phenanthrene to phenanthridone cyclization strategy: Organic Letters

J. Collins; M. Drouin; X. Sun; U. Rinner; T. Hudlicky

doi:10.1021/ol702440f

Total synthesis of 7-deoxypancratistatin-1-carboxaldehyde and carboxylic acid via solvent-free intramolecular aziridine opening: Phenanthrene to phenanthridone cyclization strategy: Organic Letters

J. Collins, M. Drouin, X. Sun, U. Rinner, T. Hudlicky

Publikation: Beitrag in Fachzeitschrift › Artikel › Begutachtung

Abstract

Solid-state silica-gel-catalyzed opening of aziridine 6 provided phenanthrene 7, whose oxidative cleavage, recyclization, and further elaboration furnished the C-1 aldehyde and carboxylic acid derivatives of 7-deoxypancratistatin for potential analogue synthesis. © 2008 American Chemical Society.

Originalsprache	Englisch
Seiten (von - bis)	361-364
Seitenumfang	4
Fachzeitschrift	Org. Lett.
Jahrgang	10
Ausgabenummer	3
DOIs	https://doi.org/10.1021/ol702440f
Publikationsstatus	Veröffentlicht - 29 Dez. 2007
Extern publiziert	Ja

Forschungsfelder

Alkaloide
Amaryllidaceae-Alkaloide
Gesamtsynthese
Stereoselektive Synthese
Struktur-Wirkungs-Beziehung

IMC Forschungsschwerpunkte

Materials science

ÖFOS 2012 - Österreichischen Systematik der Wissenschaftszweige

104015 Organische Chemie
104013 Naturstoffchemie
301305 Medizinische Chemie

UN SDGs

Dieser Output leistet einen Beitrag zu folgendem(n) Ziel(en) für nachhaltige Entwicklung

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10.1021/ol702440f

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abstract = "Solid-state silica-gel-catalyzed opening of aziridine 6 provided phenanthrene 7, whose oxidative cleavage, recyclization, and further elaboration furnished the C-1 aldehyde and carboxylic acid derivatives of 7-deoxypancratistatin for potential analogue synthesis. {\textcopyright} 2008 American Chemical Society.",

keywords = "Amaryllidaceae Alkaloids, Aziridines, Carboxylic Acids, Catalysis, Cyclization, Isoquinolines, Molecular Structure, Phenanthrenes, 7 deoxypancratistatin 1 carboxaldehyde, 7-deoxypancratistatin-1-carboxaldehyde, Amaryllidaceae alkaloid, aziridine, aziridine derivative, carboxylic acid, isoquinoline derivative, phenanthrene, phenanthrene derivative, phenanthridone, unclassified drug, article, catalysis, chemical structure, chemistry, cyclization, synthesis",

author = "J. Collins and M. Drouin and X. Sun and U. Rinner and T. Hudlicky",

note = "Export Date: 13 June 2023; Cited By: 37; Correspondence Address: T. Hudlicky; Department of Chemistry and Centre for Biotechnology, Brock University, St. Catharines, ON L2S 3A1, 500 Glenridge Avenue, Canada; email: [email protected]",

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T2 - Organic Letters

AU - Collins, J.

AU - Drouin, M.

AU - Sun, X.

AU - Rinner, U.

AU - Hudlicky, T.

N1 - Export Date: 13 June 2023; Cited By: 37; Correspondence Address: T. Hudlicky; Department of Chemistry and Centre for Biotechnology, Brock University, St. Catharines, ON L2S 3A1, 500 Glenridge Avenue, Canada; email: [email protected]

PY - 2007/12/29

Y1 - 2007/12/29

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AB - Solid-state silica-gel-catalyzed opening of aziridine 6 provided phenanthrene 7, whose oxidative cleavage, recyclization, and further elaboration furnished the C-1 aldehyde and carboxylic acid derivatives of 7-deoxypancratistatin for potential analogue synthesis. © 2008 American Chemical Society.

KW - Amaryllidaceae Alkaloids

KW - Aziridines

KW - Carboxylic Acids

KW - Catalysis

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KW - Molecular Structure

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KW - 7-deoxypancratistatin-1-carboxaldehyde

KW - Amaryllidaceae alkaloid

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KW - carboxylic acid

KW - isoquinoline derivative

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KW - phenanthrene derivative

KW - phenanthridone

KW - unclassified drug

KW - article

KW - catalysis

KW - chemical structure

KW - chemistry

KW - cyclization

KW - synthesis

U2 - 10.1021/ol702440f

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ER -