Studies on the Enantioselective Synthesis of Carbazolones as Intermediates in Aspidosperma and Kopsia Alkaloid Synthesis*
Christopher J. Gartshore A and David W. Lupton A B
+ Author Affiliations
- Author Affiliations
A School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.
B Corresponding author. Email: david.lupton@monash.edu
Australian Journal of Chemistry 66(8) 882-890 https://doi.org/10.1071/CH13287
Submitted: 3 June 2013 Accepted: 5 July 2013 Published: 12 August 2013
Abstract
Two strategies for the assembly of homochiral carbazolones have been investigated. The first exploited desymmetrisation of 1,3-cyclohexadione derivatives however this failed to deliver satisfactory outcomes. An orthogonal route exploiting palladium catalysed decarboxylative allylation of racemic carbazolone β-ketoesters has been developed. Herein we report full details on the development of this reaction and clarify apparent discrepancies between our preliminary reports and those of Shao.
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