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Synlett 1995; 1995(1): 27-28
DOI: 10.1055/s-1995-4869
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A Novel Approach to the Ergot Alkaloid Skeleton

Sabine Barbey, John Mann*
  • *Department of Chemistry, Reading University, Whiteknights, P.O. Box 224, RG6 2AD Reading, England
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Publication History

Publication Date:
31 December 2000 (online)

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We describe a ten stage synthesis of an advanced intermediate for elaboration into ergot alkaloids, from 4-carbomethoxyindole. The key step involved an intramolecular cyclisation involving the allyl cation derived from N-benzenesulphonyl, 3-(3’-methoxyprop-2’-en-1’-yl), 4-(1’-hydroxy-2’-trimethylsilylmethyl-prop-2’-en-1’-yl)-indole.

intramolecular [3+2] cycloaddition - allyl cation

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