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

Research output: Contribution to journalArticle

33 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 languageEnglish
Pages (from-to)361-364
Number of pages4
JournalOrganic Letters
Volume10
Issue number3
DOIs
Publication statusPublished - Feb 7 2008

Fingerprint

phenanthrene
Cyclization
Silica Gel
silica gel
Carboxylic Acids
aldehydes
Aldehydes
carboxylic acids
cleavage
analogs
Derivatives
solid state
acids
synthesis
phenanthridone
7-deoxypancratistatin
7-deoxypancratistatin-1-carboxaldehyde
aziridine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Total synthesis of 7-deoxypancratistatin-1-carboxaldehyde and carboxylic acid via solvent-free intramolecular aziridine opening : Phenanthrene to phenanthridone cyclization strategy. / Collins, Jonathan; Drouin, Melissa; Sun, Xuetong; Rinner, Uwe; Hudlicky, Tomas.

In: Organic Letters, Vol. 10, No. 3, 07.02.2008, p. 361-364.

Research output: Contribution to journalArticle

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