几种多卤代蕨藻单萜的对映选择性发散合成及其对实体瘤的选择性评估。
Enantioselective divergent syntheses of several polyhalogenated Plocamium monoterpenes and evaluation of their selectivity for solid tumors.
作者信息
Vogel Carl V, Pietraszkiewicz Halina, Sabry Omar M, Gerwick William H, Valeriote Frederick A, Vanderwal Christopher D
机构信息
1102 Natural Sciences II, Department of Chemistry, University of California, Irvine, Irvine, CA 92697 (USA).
出版信息
Angew Chem Int Ed Engl. 2014 Nov 3;53(45):12205-9. doi: 10.1002/anie.201407726. Epub 2014 Sep 12.
Abstract
The family of polyhalogenated monoterpenes from Plocamium counts over a hundred known members. Using glyceraldehyde acetonide as a chiral-pool precursor, an enantioselective and divergent strategy was developed that provides a blueprint for the synthesis of many of the small yet complex acyclic members of this family. The broad applicability of this approach is demonstrated with the short, eight-step synthesis of four natural products and three analogues. These syntheses are the first of any members of the acyclic polyhalogenated Plocamium monoterpenes and permitted the evaluation of their selectivity against a range of tumor cell lines.
摘要
来自扁枝藻属的多卤代单萜类化合物家族有超过一百个已知成员。以丙酮缩甘油醛作为手性源前体，开发了一种对映选择性和发散性策略，为该家族中许多小而复杂的无环成员的合成提供了蓝图。通过四种天然产物和三种类似物的八步短合成，证明了该方法的广泛适用性。这些合成是无环多卤代扁枝藻属单萜类化合物任何成员的首次合成，并允许评估它们对一系列肿瘤细胞系的选择性。
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