Organic Letters 2008-02-07

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

Index: Org. Lett. 10(3) , 361-4, (2008)

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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.