Synthesis of Carbocycles via Intramolecular Conjugate Additions: Total Syntheses of Axane Sesquiterpenoids

Syntheses of (+/-)-axamide-1 (2) and (+/-)-axisonitrile-1 (1) are described. The syntheses require 12 steps and 13 steps, respectively, from vinylogous ester 8 and feature the diastereoselective cyclization of unsaturated ester 7 to perhydroindan 5. Some interesting reactions of the organometallic derived from [(trimethylsilyl)methyl]magnesium chloride and cerium trichloride are also described.