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Oxidative cyclization of morusin
Author(s) -
Nomura Taro,
Fukai Toshio,
Matsumoto Junko
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170404
Subject(s) - chemistry , rose bengal , oxidizing agent , hematoporphyrin , singlet oxygen , photochemistry , oxidative phosphorylation , electron transfer , radical , oxygen , medicinal chemistry , organic chemistry , photodynamic therapy , biochemistry
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‐ t ‐butylphenol, a radical quencher, to give compounds (IV, V, VI and VII) coupled with the 2,4,6‐tri‐ t ‐butylphenoxy radical. On the basis of above results, the possible mechanism of this oxidative cyclization was discussed. In addition, morusin hydroperoxide (II) was also obtained by photo‐sensitized oxidation of morusin (I) in the presence of sensitizers (Rose Bengal, hematoporphyrin). To elucidate the reaction mechanism similar reactions were carried out in the presence of radical quencher (2,4,6‐tri‐ t ‐butylphenol) or singlet oxygen quencher (triethylenediamine). From these results, the possible mechanism of the formation of morusin hydroperoxide (II) from morusin (I) was discussed.