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

被引：31

作者：

Toumi, Mathieu ^{[1
]}

Rincheval, Vincent ^{[2
]}

Young, Ashley ^{[3
]}

Gergeres, Danielle ^{[3
]}

Turos, Edward ^{[3
]}

Couty, Francois ^{[1
]}

Mignotte, Bernard ^{[2
]}

Evano, Gwilherm ^{[1
]}

机构：

[1] Univ Versailles St Quentin Yvelines PRES UniverSu, Inst Lavoisier Versailles, CNRS, UMR 8180, F-78035 Versailles, France

[2] Univ Versailles St Quentin Yvelines PRES UniverSu, Lab Genet & Biol Cellulaire, CNRS, UMR 8159, F-78035 Versailles, France

[3] Univ S Florida, Dept Chem, Ctr Mol Divers Drug Design Discovery & Delivery, Tampa, FL 33620 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 20期

关键词：

Alkaloids; Biological activity; Copper catalysis; Cyclopeptide alkaloids; Macrocycles; Total synthesis; RING-CLOSING METATHESIS; MEDIATED COUPLING REACTIONS; ALPHA-AMINO ACRYLAMIDE; PEPTIDE ALKALOIDS; SANJOININE G1; ARYL HALIDES; STRAIGHTFORWARD SYNTHESIS; ALIPHATIC-ALCOHOLS; FACILE SYNTHESIS; VINYL HALIDES;

D O I：

10.1002/ejoc.200900122

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：3368 / 3386

页数：19

共 84 条

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