厦霉素 A、C、F、H 和奥里达霉素 A 的全合成及抗真菌活性初步评价。
Total Syntheses of Xiamycins A, C, F, H and Oridamycin A and Preliminary Evaluation of their Anti-Fungal Properties.
机构信息
Department of Chemistry, University of California, Berkeley, CA, 94720, USA.
Corteva Agriscience, Crop Protection Discovery, Zionsville, IN, 46077, USA.
出版信息
Angew Chem Int Ed Engl. 2019 Oct 21;58(43):15304-15308. doi: 10.1002/anie.201908399. Epub 2019 Sep 12.
Abstract
Divergent and enantiospecific total syntheses of the indolosesquiterpenoids xiamycins A, C, F, H and oridamycin A have been accomplished. The syntheses, which commence from (R)-carvone, employ a key photoinduced benzannulation sequence to forge the carbazole moiety characteristic of these natural products. Late-stage diversification from a common intermediate enabled the first syntheses of xiamycins C and F, and an unexpected one-pot oxidative decarboxylation, which may prove general, led to xiamycin H. All synthetic intermediates and the natural products were tested for anti-fungal activity. Xiamycin H emerged as an inhibitor of three agriculturally relevant fungal pathogens.
摘要
已经完成了吲哚倍半萜类化合物 xiamycins A、C、F、H 和 oridamycin A 的非对映和对映选择性的全合成。这些合成方法从（R）-香芹酮开始，采用关键的光诱导苯并环化序列来构建这些天然产物特有的咔唑部分。从一个共同的中间体进行的后期多样化使得 xiamycins C 和 F 的首次合成成为可能，并且可能证明是通用的意外一锅氧化脱羧作用导致了 xiamycin H 的产生。所有的合成中间体和天然产物都进行了抗真菌活性测试。xiamycin H 作为三种农业相关真菌病原体的抑制剂出现。
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