A brief synthesis of (-)-englerin A |
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Authors: | Li Zhenwu Nakashige Mika Chain William J |
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Institution: | Department of Chemistry, 2545 The Mall, University of Hawaii at Manoa, Honolulu, Hawaii 96822, USA. |
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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. |
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