Total Syntheses of Xiamycins A,C, F,H and Oridamycin A and Preliminary Evaluation of their Anti‐Fungal Properties |
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Authors: | Magnus Pfaffenbach Ian Bakanas Nicholas R. O'Connor Jessica L. Herrick Richmond Sarpong |
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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. |
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Keywords: | Benzanellierung Chiraler Pool Divergente Synthese Fungitoxizitä t Totalsynthese |
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