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Communication | Regular issue | Vol 6, No. 11, 1977, pp.1847-1854
Published online, 1st January, 1970
DOI: 10.3987/R-1977-11-1847
Oxidative Cyclization of Morusin with Manganese Dioxide

Taro Nomura,* Toshio Fukai, and Masa Katayanagi

*School of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan


Oxidative cyclization of morusin (I) by using one-electron transfer oxidizing agents (manganese dioxide, silver oxide) afforded morusin hydroperoxide (II). A similar reaction was carried out in the presence of 2,4,6-tri-tert-butylphenol, a radical quencher, to give compounds (V-VIII) coupled with the 2,4,6-tri-tert-butylphenoxy radical. On the basis of above results, the possible mechanism of this oxidative cyclization was discussed. In addition, cyclomorusin (III) and XI were obtained from I with manganese dioxide in a nitrogen atmosphere.