Structure and total synthesis of (-)-myrionidine and (-)-schoberine, antimalarial alkaloids from Myrioneuron nutans. - Université Claude Bernard Lyon 1 Accéder directement au contenu
Article Dans Une Revue Journal of Organic Chemistry Année : 2008

Structure and total synthesis of (-)-myrionidine and (-)-schoberine, antimalarial alkaloids from Myrioneuron nutans.

Résumé

Two new alkaloids, (5S,9S,10R)-myrionidine (1) and (5S,9S,10R,13S)-myrionamide (2), along with the known schoberine (3), were isolated from the leaves of Myrioneuron nutans (Rubiaceae), and their structures were determined from spectral analysis, including mass spectrometry and 2D NMR. The total asymmetric syntheses of (-)-myrionidine (1), (-)-schoberine (3), their enantiomers as well as their 9-epimers derivatives were performed, allowing the determination of their absolute configuration together with that of myrionamide (2). (-)-Myrionidine (1) and its synthetic enantiomer (18) showed a significant antimalarial activity on Plasmodium falciparum.

Dates et versions

hal-00337326 , version 1 (06-11-2008)

Identifiants

Citer

van Cuong Pham, Akino Jossang, Philippe Grellier, Thierry Sévenet, van Hung Nguyen, et al.. Structure and total synthesis of (-)-myrionidine and (-)-schoberine, antimalarial alkaloids from Myrioneuron nutans.. Journal of Organic Chemistry, 2008, 73 (19), pp.7565-73. ⟨10.1021/jo801046j⟩. ⟨hal-00337326⟩
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