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Synlett 2016; 27(01): 146-150
DOI: 10.1055/s-0035-1560519
letter
© Georg Thieme Verlag Stuttgart · New York

Synthetic Studies on Psychotrimine: Palladium-Catalysed Arylation of 2-(N-Indolyl) Amides

Emma L. Watson
a   Institute of Process Research and Development and School of Chemistry, University of Leeds, Leeds LS2 9JT, UK   Email: s.p.marsden@leeds.ac.uk
,
Anthony Ball
a   Institute of Process Research and Development and School of Chemistry, University of Leeds, Leeds LS2 9JT, UK   Email: s.p.marsden@leeds.ac.uk
,
Steven A. Raw
b   AstraZeneca, Chemical Development, Charter Way, Silk Road Business Park, Macclesfield SK10 2NA, UK
,
Stephen P. Marsden*
a   Institute of Process Research and Development and School of Chemistry, University of Leeds, Leeds LS2 9JT, UK   Email: s.p.marsden@leeds.ac.uk
› Author Affiliations
Further Information

Publication History

Received: 02 October 2015

Accepted after revision: 14 October 2015

Publication Date:
09 November 2015 (online)

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Dedicated to Professor Steve Ley FRS on the occasion of his 70th birthday

Abstract

Through careful choice of conditions, 2-(N-indolyl) amides can be directed to undergo selectively either enolate arylation to give oxindoles or direct arylation to give indolo-fused benzodiazepines. The former chemistry facilitates the synthesis of the hexahydropyrrolindole core of psychotrimine.

Key words

alkaloids - arylation - cyclisation - polycycles - total synthesis
 

  • References and Notes

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