Abstract
The cycloaddition of methyl cis-2-amino- trans-6-methylcyclohexanecarboxylate ( 3) with 1-p-(toluenesulfonyl)-1-pentyne ( 4) afforded the corresponding enaminone 2, that was in turn reduced to (±)-pumiliotoxin C ( 1). The acetylenic sulfone 4 thus functions as the synthetic equivalent of the alkene dipole 5 in this process.
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