title: A brief synthesis of (-)-englerin A.
abstract: 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.
authors.affiliation: Department of Chemistry, 2545 The Mall, University of Hawaii at Manoa, Honolulu, Hawaii 96822, USA.
authors.forename: Zhenwu
authors.initials: Z
authors.lastname: Li
authors.forename: Mika
authors.initials: M
authors.lastname: Nakashige
authors.forename: William J
authors.initials: WJ
authors.lastname: Chain
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis; D006801:Humans; D007680:Kidney Neoplasms / Q000188:drug therapy; D029803:Phyllanthus / Q000737:chemistry*; D045789:Sesquiterpenes, Guaiane / Q000138:chemical synthesis*
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D045789:Sesquiterpenes, Guaiane; C534971:englerin A; C551614:englerin B