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Synthesis 1991; 1991(12): 1089-1094
DOI: 10.1055/s-1991-28397
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Nickel(0)-Catalyzed Intramolecular [4 + 4] Cycloadditions: 5. The Type II Reaction in the Synthesis of Bicyclo[5.3.1]undecadienes

Paul A. Wender* , Mark J. Tebbe
  • *Department of Chemistry, Stanford University, Stanford, CA 94 305, USA
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Publication Date:
29 April 2002 (online)

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The preparation and type II intramolecular [4 + 4] cycloaddition of a bis-diene is described in connection with studies on the synthesis of taxol (1), crispolide (2), and vulgarolide (3). The required bis-diene is prepared by a carboalumination of an alkyne, giving an iodide which is then coupled in the presence of palladium to a vinyltin to give a stereodefined diene. Elaboration of this system involves the reaction of 2-lithio-1, 3-butadiene with a dienal to give a bis-1,3-diene tethered at the terminus of one diene and the internal position of the other. Cycloaddition of this bis-diene mediated by a nickel(0)/tri-o-biphenyl phosphite catalyst provides a bicyclo[5.3.1]undecadiene, a ring system common to a variety of complex molecules.