Department of Chemistry, 2545 The Mall, University of Hawaii at Manoa, Honolulu, Hawaii 96822, USA.
J Am Chem Soc. 2011 May 4;133(17):6553-6. doi: 10.1021/ja201921j. Epub 2011 Apr 8.
Englerins A and B are guaiane sesquiterpenes that were isolated from the bark of Phyllanthus engleri, a plant indigenous to east Africa. The englerins consist of a 5-6-5 fused tricyclic structure with an ether bridge and two ester-bearing stereogenic centers, including a highly unusual glycolate residue. Englerin A is a potent and selective inhibitor of the growth of six human renal cancer cell lines. We report herein an efficient, eight-step synthesis of englerin A that leverages simple carbonyl-enabled carbon-carbon bond formations. Our route is amenable to the production of a diverse series of analogues for structure-function studies and determination of the mode of action of these natural products.
埃格林 A 和 B 是从非洲东部特有的 Phyllanthus engleri 树皮中分离出来的愈创木烷倍半萜。埃格林由具有醚桥和两个带酯基的手性中心的 5-6-5 稠合三环结构组成，包括一个非常不寻常的乙醇酸盐残基。埃格林 A 是一种有效的选择性抑制剂，可以抑制六种人肾癌细胞系的生长。我们在此报告了一种高效的、八步合成埃格林 A 的方法，该方法利用简单的羰基促进的碳-碳键形成。我们的路线适合生产多种类似物，用于结构-功能研究和确定这些天然产物的作用模式。
