- Convenient synthesis of 2,3,9,10-tetraoxygenated protoberberine alkaloids and their 13-methyl alkaloids
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New and convenient synthesis of 2,3,9,10-tetraoxygenated protoberberine alkaloids and their 13-methyl alkaloids through the same intermediates was developed. Acylation of the brominated benzylphenethylamine (13) with α- chloro-α-(methylthio)acetyl chloride, followed by cyclization with stannic chloride, furnished the key intermediates 4-methylthio-3- phenethylisoquinolin-3-ones (14), which were methylated to provide their methyl derivatives (17). Both isoquinolin-3-ones (14, 17) were easily transformed into protoberberine alkaloids (16) and their 13-methyl alkaloids (21) in good yield.
- Hanaoka, Miyoji,Hirasawa, Taeko,Cho, Won Jea,Yasuda, Shingo
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p. 399 - 404
(2007/10/03)
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- A NEW AND CONVENIENT SYNTHESIS OF PROTOBERBERINE ALKALOIDS: (+/-)-TETRAHYDROPALMATINE, (+/-)-SINACTINE, (+/-)-CANADINE AND-)-STYLOPINE
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2,3,9,10-Tetraoxygenated protoberberine alkaloids (14) were efficiently synthesized from the readily available benzaldehyde (2 or 10) via the benzylphenethylamines (11) and 2-phenethylisoquinolin-3-ones (12 or 13).
- Yasuda, Shingo,Hirasawa, Taeko,Hanaoka, Miyoji
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p. 2399 - 2402
(2007/10/02)
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