期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 58, 期 43, 页码 15304-15308出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201908399
关键词
benzannulation; chiral pool; divergent synthesis; fungitoxicity; total synthesis
资金
- Corteva Agriscience
- National Institutes of Health [NIGMS R35 GM130345]
- Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) [PF 910/1-1]
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.
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