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Development of the [3 + 2] Annulations of Cyclohexenylsilanes and Chlorosulfonyl Isocyanate: Application to the Total Synthesis of (±)-Peduncularine

2002; American Chemical Society; Volume: 124; Issue: 38 Linguagem: Inglês

10.1021/ja012152f

1943-2984

Claudia W. Roberson, K. A. Woerpel,

Synthetic Organic Chemistry Methods

The synthesis of (+/-)-peduncularine was accomplished using the [3 + 2] annulation of an allylic silane with chlorosulfonyl isocyanate to assemble the bicyclic core of the alkaloid. The stereochemistry of the annulation product was employed to control the installation of the indolylmethyl side chain at C-7 with complete stereoselectivity.