An O-to-N intramolecular acyl migration in C19-diterpenoid alkaloids

作者:Chen, Qi-Feng; Jian, Xi-Xian; Chen, Qiao-Hong; Wang, Feng-Peng*
来源:Journal of Asian Natural Products Research, 2012, 14(6): 586-591.
DOI:10.1080/10286020.2012.680444

摘要

The O-acyl group at C-1 of two C-19-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 C-19-diterpenoid alkaloids, which is consistent with the conformation of rings A and E in the C-19-diterpenoid alkaloids.

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