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Four novel taxoid analogs were conversionally synthesized from the C19-diterpenoid alkaloid deltaline, and their cytotoxic activities were evaluated against a small panel of cancer cell lines. [ABSTRACT FROM AUTHOR]

The regioselective demethylations of two C19-diterpenoid alkaloids, 2 and 3, have been achieved with HBr-HOAc, trimethylsilyl iodide, or BBr3. It was observed that HBr-HOAc is an optimal demethylating agent for these two C19-diterpenoid alkaloids because it could provide different O-demethylation products by using different reaction temperature and reaction time. Especially, 1-O-methyl group in 2 and 3, one of the most difficult ones to be demethylated, could be removed by the treatment with HBr-HOAc at an elevated temperature and a prolonged reaction time. [ABSTRACT FROM AUTHOR]

The conversional synthesis of taxoids by the BAC sequence from the C19-diterpenoid alkaloids, 14-acetyltalatisamine (1), yunaconitine (12), and 14-acetylchasmanine (19), was designed and explored. Two aconane-type diterpenes 17 and 28, the advanced intermediates for our conversional synthesis, were synthesized. The key steps include the rupture of the C(7)-C(17) bond, the formation of imine, and the denitrogenation. [ABSTRACT FROM AUTHOR]

Following the report on the synthesis of the 7,17-seco compounds [Wang, F.P., Yang, J.S., Chen, Q.H., Yu, L. and Li, B.G. (2000), Chem. Pharm. Bull. 48, 1912-1916], further studies on the reaction optimization for cleavage of the C(7),C(17) bond led to the 7,17-seco norditerpenoid alkaloids (e.g. 4, 9) in nearly 90% yield. [ABSTRACT FROM AUTHOR]

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]

The first biomimetic conversion from the aconitine-type C19-diterpenoid alkaloids to the corresponding alkaloids of lactone-type C19-diterpenoid alkaloid has been achieved. Chasmanine was used as starting material with Baeyer–Villiger oxidation as a key reaction. It was also observed that the oxygenated group at C-16 did not change the relative migration tendencies of C-13 and C-9 during the oxidation. Meantime, a novel D-ring fragmented compound was obtained during the course of the present investigation. The plausible mechanism of the formation of this compound was also proposed. [ABSTRACT FROM AUTHOR]

Treatment of some C19-diterpenoid alkaloids (3, 6, 10 and 12) with anhydrous DMSO at 100-170°C for 3-7 h led to the formation of the corresponding imines (4, 7/8, 11, 13/14) in 65-83% yield, respectively. This is a new simpler formation of the imines of the C19-diterpenoid alkaloids. [ABSTRACT FROM AUTHOR]

A new franchetine-type (leueandine 1 ) and two new lycoctonine-type [potanisines F ( 3 ) and G ( 5 )] C 19 -diterpenoid alkaloids have been isolated from the roots of Aconitum hemsleyanum var. leueanthus and Delphinium potaninii , respectively, and their structures were established on the basis of spectral data. [ABSTRACT FROM AUTHOR]