Total syntheses of the sesquiterpenoids (±)-axamide-1, (±)-axisonitrile-1, and the corresponding C-10 epimers

Abstract
Total syntheses of (.+-.)-axamide-1 (1), (.+-.)-axisonitrile-1 (2), and the corresponding C-10 epimers 16 and 17 are described. The key steps of the synthetic sequence involve methylenecyclohexane annulation of 2-methyl-2-cyclopenten-1-one and TiCl4-catalyzed conjugate addition of 3-methyl-1-1,bis(trimethylsiloxy)-1-butene to the bicyclic enone 8.

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