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

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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.
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Keywords: 15α-hydroxylneoline; C19-diterpenoid alkaloid; intramolecular acyl migration; neoline

Document Type: Research Article

Affiliations: Department of Chemistry of Medicinal Natural Products,West China College of Pharmacy, Sichuan University, Chengdu,610041, China

Publication date: June 1, 2012

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