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Communication | Special issue | Vol 5, No. 1, 1976, pp.175-182
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0175
Phenol Oxidation of Isoquinoline Alkaloids with Cuprous Chloride and Oxygen in Pyridine as an Enzymatic Model. Biomimetic Total Synthesis of Corytuberine, Isoboldine, Pallidine, Orientalinone and Kreysiginone

Tetsuji Kametani,* Yoshinori Satoh, Makoto Takemura, Yohko Ohta, Masataka Ihara, and Keiichiro Fukumoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Phenol oxidation of (+)-reticuline (1) perchlorate with cuprous chloride and oxygen in pyridine gave (+)-corytuberine (2), (+)-isoboldine (3), and pallidine (4). Under the same reaction conditions, (±)-orientaline (5) perchlorate yielded (±)-orientalinone (6) and its epimer (7), while (±)-1,2,3,4-tetrahydro-7-hydroxy-1-(4-hydroxy-3-methoxyphenethyl)-6-methoxyisoquinoline (8) hydrochloride furnished (±)-kreysiginone (9) and the diastereoisomer (10). Oxidation with cupric chloride and potassium superoxide in pyridine gave rise to the similar results.