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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
Author(s) -
Toumi Mathieu,
Rincheval Vincent,
Young Ashley,
Gergeres Danielle,
Turos Edward,
Couty François,
Mignotte Bernard,
Evano Gwilherm
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900122
Subject(s) - chemistry , intramolecular force , total synthesis , stereochemistry , iodide , combinatorial chemistry , organic chemistry
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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)