Chemistry Letters, Vol.29, No.5, 512-513, 2000
2-aryl-5-epoxynitrile anion cyclizations: Total syntheses of (+/-)-alpha-cuparenone and (+/-)-epilaurene
Total syntheses of the cyclopentane sesquiterpenes of the title using an epoxynitrile anion cyclization reaction as key step, are described. The preferential formation of the cyclopentane ring from a terminal disubstituted 5-epoxynitrile (e.g. 2b) had not previously been observed. The 2-aryl substituent is reasonably assumed to be responsible for this divergence.