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Synlett 1999; 1999(4): 501-503
DOI: 10.1055/s-1999-2621
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A Short Synthesis of γ-Lycorane using Ni/AcOH Mediated Radical Cyclisation

Jérôme Cassayre* , Samir Z. Zard
  • *Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-Sur-Yvette, France; Fax +33(0)1 69 33 30 10; E-mail: sam.zard@icsn.cnrs-gif.fr.
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Publication Date:
31 December 1999 (online)

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A short synthesis of (±)-γ-lycorane 6 is described using two different radical cyclisations. The key step is the formation of tetrahydroindolone 9 by a nickel-promoted 5-endo radical cyclisation. This is followed by a tributylstannane-mediated 6-endo ring closure to the tetracyclic lactam 10 which is readily reduced to (±)-γ-lycorane 6.

γ-lycorane - nickel - radical cyclisation