The Total Synthesis of - -Balanol

Abstracted with permission from J. Org. Chem., 1994,59, 5147 and J. Am. Chem. Soc., 1994,116, 8402 1994 American Chemical Society 

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The total synthesis of balanol, a fungal metabolite was accomplished by K.C. Nicolaou et al. For the construction of the central hexahydroazepine ring, they have utilized a 7-exo-tet cyclization. The substitution reaction between the mesylate of the primary alcohol and the Cbz-protected amine was effected by a slight excess of base to produce the desired 7-membered ring in high yield. 

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