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

Jonathan Collins; Melissa Drouin; Xuetong Sun; Uwe Rinner; Tomas 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

Jonathan Collins, Melissa Drouin, Xuetong Sun, Uwe Rinner, Tomas Hudlicky^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

37 Citations (Scopus)

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.

Original language	English
Pages (from-to)	361-364
Number of pages	4
Journal	Organic Letters
Volume	10
Issue number	3
DOIs	https://doi.org/10.1021/ol702440f
Publication status	Published - Feb 7 2008

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol702440f

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title = "Total synthesis of 7-deoxypancratistatin-1-carboxaldehyde and carboxylic acid via solvent-free intramolecular aziridine opening: Phenanthrene to phenanthridone cyclization strategy",

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.",

author = "Jonathan Collins and Melissa Drouin and Xuetong Sun and Uwe Rinner and Tomas Hudlicky",

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journal = "Organic Letters",

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T2 - Phenanthrene to phenanthridone cyclization strategy

AU - Collins, Jonathan

AU - Drouin, Melissa

AU - Sun, Xuetong

AU - Rinner, Uwe

AU - Hudlicky, Tomas

PY - 2008/2/7

Y1 - 2008/2/7

N2 - 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.

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.

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JF - Organic Letters

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

Abstract

ASJC Scopus subject areas

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