4-Methylenedioxolan-2-ones as convenient synthons for the preparation of natural products of the berbine and calycotomine series |
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| Authors: | I. Yu. Titov N. B. Chernysheva Yu. B. Chudinov A. A. Bogolyubov V. V. Semenov |
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| Affiliation: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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| Abstract: | Intramolecular amidoalkylation of nonactivated 3-(2-arylethyl)-4-hydroxyoxazolidin-2-ones in polyphosphoric acid gave oxazolo[4,3-a]isoquinolin-3-one whose hydrolysis affords isoquinoline β-amino alcohols, calycotomine analogs. Using the developed procedure, 13,13,13a-trimethylberbine was synthesized. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 548–554, March, 2006. |
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| Keywords: | β -amino alcohols 4-hydroxyoxazolidin-2-ones 1,5,6,10b-tetrahydrooxazolo[4,3-a]isoquinolin-3-ones intramolecular amidoalkylation calycotomine 13,13,13a-tri-methylberbine alkaloids polyphosphoric acid carbamates |
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