A general route to cyclopeptide alkaloids: total syntheses and biological evaluation of paliurines e and F, ziziphines N and Q, abyssenine A, mucronine E, and analogues

Vincent Rincheval (1, 2) , Bernard Mignotte (1, 2) , François Couty (1, 3) , Gwilherm Evano (1, 3) , Danielle A. Gergeres , Ashley Young , Mathieu Toumi (1, 3) , Edward Turos

1 Université Paris-Saclay
2 LGBC - Laboratoire de génétique et biologie cellulaire
3 ILV - Institut Lavoisier de Versailles

A full account of the total syntheses of the cyclopeptide alkaloids paliurine E and F, ziziphine N and Q, abyssenine A, and mucronine E is provided. A key feature of the syntheses involves an intramolecular amidation of a vinyl iodide, which allows us simultaneously to address two synthetic challenges associated with cyclopeptide alkaloids: the formation of the enamide and macrocyclization. We also document the use of other strategies for the macrocyclization step, as well as the evaluation of the antibacterial and cytotoxic properties of the natural products and analogues obtained. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

Mots clés: facile synthesis; copper catalysis; aryl halides; macrocycles; total synthesis; biological activity; cyclopeptide alkaloids; ring-closing metathesis; mediated coupling reactions; vinyl halides; straightforward synthesis; alpha-amino acrylamide; peptide alkaloids; sanjoinine g1; aliphatic-alcohols; facile synthesis; alkaloids

Domaines: Chimie

Vincent Rincheval, Bernard Mignotte, François Couty, Gwilherm Evano, Danielle A. Gergeres, et al.. A general route to cyclopeptide alkaloids: total syntheses and biological evaluation of paliurines e and F, ziziphines N and Q, abyssenine A, mucronine E, and analogues. European Journal of Inorganic Chemistry, 2009, pp.3368-3386. ⟨10.1002/ejoc.200900122⟩. ⟨hal-04017655⟩