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Synlett 1992; 1992(9): 766-768
DOI: 10.1055/s-1992-21488
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Allylsilane-Terminated Approach to Calicheamicin Model Systems

Dieter Schinzer* , Jazid Kabbara
  • *Institut für Organische Chemie der Technischen Universität Braunschweig, Hagenring 30, D-3300 Braunschweig, Germany
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Publication Date:
08 March 2002 (online)

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An organometallic route to bicyclic enediynes using iron-, copper-, silicon-, and palladium-mediated reactions is reported. The key step involves a Lewis acid promted Sakurai reaction of a conjugated allylsilane 7, which proceeded regio- and stereo-specifically. The bicyclic cross-conjugated enediyne 10 (12,12-ethylenedioxy-8-methylenebicyclo[8.3.1]tridec-4-ene-2,6-diyne) represents a model compound for the DNA cleaving calicheamicins.

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