Aniba neolignans from

ARAtiJO Lima, O., O. R. Gottlieb, and M. T. Magalhaes The Chemistry of Brazilian Lauraceae. XX. Burchellin, a Neolignan from Aniba burchellii. Phytochem. 11, 2031 (1972). 

Dias, S. M., J. B. Fernandes, O. R. Gottlieb, and J. G. S. Maia Neolignans from a Species of the Genus Aniba. Communication presented at the XXVII Annual Meeting of Sociedade Brasileira para o Progresso da Ciencia, Belo Horizonte (1975). 

Gottlieb, O. R., M. L. da Silva, and Z. S. Ferreira The Chemistry of Brazilian Lauraceae. XXXI. Neolignans from Aniba terminalis. Phytochem. 14 1825 (1975). 

Fernandes J B, Gottlieb O R 1976 Neolignans from Aniba species. Phytochemistry 15 1033-1036... 

Dias SMC, Fernandes J B, Maia J G S, Gottlieb O R, Gottlieb H E 1986 The chemistry of Brazilian Lauraceae. LXXVII. Eusiderins and other neolignans from an Aniba species. Phytochemistry 25 213-217... 

Trevisan L M V, Yoshida M, Gottlieb O R 1984 The chemistry of Brazilian Lauraceae. LXXIV. Neolignans from Aniba citrifolia. Phytochemistry 23 701... 

Martinezv JC, Maia JGS, Yoshida M, Gottlieb OR 1980 Chemistry of Brazilian Lauraceae. 55. Neolignans from Aniba species. Phytochemistry 19 474-476... 

In a series of synthetic studies on these neolignans, 2-allyl-4,5-dimethoxyphenol (147) was submitted to constant current or controlled potential electrolysis in 90% aq. MeCN, MeOH and 2 1 MeOH-AcOH containing excess trani-isosafrole to afford 2-allyl-5-methoxy-p-benzoquinone (148), 2-allyl-4,4,5-trhnethoxycyclohexa-2,5-dienone (149) and one of the Aniba neohgnans (150) in 83, 87 and 81% yields, respectively. Here, the neolig-nan 150 is formed selectively by a cationic [5 4- 2] cycloaddition. The use of c/5-safrole instead of the frawi-isomer provided an exo-addition product 151 and futoenone 152 in 25 and 15% yields, respectively , as shown in Scheme 29. 152 must be produced from the initially formed ewrfo-addition product 153. 

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