Total synthesis of (±)-hirsutine: application of phosphine-catalyzed imine-allene [4 + 2] annulation.

Org Lett

Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095-1569, USA.

Published: September 2012

The total synthesis of the indole alkaloid hirsutine has been achieved, with a key step being the application of our phosphine-catalyzed [4 + 2] annulation of an imine with ethyl α-methylallenoate. From commercially available indole-2-carboxaldehyde, the target was synthesized in 14 steps and 6.7% overall yield.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3439149PMC
http://dx.doi.org/10.1021/ol302077nDOI Listing

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