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Synlett 2001; 2001(9): 1428-1430
DOI: 10.1055/s-2001-16782
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Novel Use of a Selenoalkyne Within Untraditionally Mild Dötz Benzannulation Processes; Total Synthesis of a Calceolaria andina L. Natural Hydroxylated Naphthoquinone

John J. Caldwell* , Robert Colman, William J. Kerr, Euan J. Magennis
  • *Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, G1 1XL, Scotland, U.K.; Fax + 44 141 548 4246; E-mail: w.kerr@strath.ac.uk
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Publikationsdatum:
28. August 2001 (online)

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A total synthesis of the Calceolaria andina L. extract 2-(1,1-dimethyl-2-propenyl)-3-hydroxy-1,4-naphthalenedione is described incorporating the first reported Dötz benzannulation of a selenoalkyne. Importantly, it has been shown that it is possible to effect this annulation at ambient temperature under dry state conditions with a significant improvement in cyclisation yield.

carbene complexes - chromium - Dötz benzannulation - dry state techniques - selenium

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