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1. An O -to- N intramolecular acyl migration in C 19 -diterpenoid alkaloids.

Author

Chen, Qi-Feng, Jian, Xi-Xian, Chen, Qiao-Hong, and Wang, Feng-Peng

Subjects
ALKALOIDS, CHEMISTRY, MASS spectrometry, MOLECULAR structure, NUCLEAR magnetic resonance spectroscopy, PHARMACEUTICAL chemistry, RESEARCH funding, TERPENES
Abstract

The O-acyl group at C-1 of two C19-diterpenoid alkaloids 2 and 5 was transferred to the secondary amine nitrogen to form amides 3 and 6 in the basic condition. This kind of O-to-N intramolecular acyl migration could be caused by the near distance between the nucleophilic nitrogen atom and the carbonyl group of the ester at C-1 in the C19-diterpenoid alkaloids, which is consistent with the conformation of rings A and E in the C19-diterpenoid alkaloids. [ABSTRACT FROM AUTHOR]

Published
2012
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