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Synlett 1999; 1999(12): 1966-1968
DOI: 10.1055/s-1999-2979
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The Triumph of Zinc: A Short and Highly Efficient Synthesis of the Calyculin C1-C9 Tetraene Building Block by Negishi Coupling

Petri M. Pihko* , Ari M. P. Koskinen
  • *Department of Chemistry, University of Oulu, P.O.B. 3000, FIN-90401 Oulu, Finland; Fax + 358 9 451 2538; E-mail: Ari.Koskinen@hut.fi
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Publication Date:
31 December 1999 (online)

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A short and highly efficient synthesis of phosphonate 5, a key building block of the C1-C9 tetraene fragment of calyculins and calyculinamides, has been achieved. The key step involves a novel, highly chemoselective Negishi coupling with a bismetallic reagent 13.

Negishi coupling - calyculins - polyenes - Stille coupling - palladium-catalyzed cross-coupling