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Journal of Asian Natural Products Research Volume 14, 2012 - Issue 6
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Original Articles

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

Qi-Feng Chen Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu, 610041, China
,
Xi-Xian Jian Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu, 610041, China
,
Qiao-Hong Chen Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu, 610041, China
&
Feng-Peng Wang Department of Chemistry of Medicinal Natural Products, West China College of Pharmacy, Sichuan University, Chengdu, 610041, ChinaCorrespondence[email protected]
Pages 586-591 | Received 13 Feb 2012, Accepted 26 Mar 2012, Published online: 09 May 2012
 
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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.

Acknowledgment

We are grateful to the National Natural Science Foundation of China (No. 30873147) for financial support of this research.

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