Total syntheses of the strobilurins G, M, and N |
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Authors: | Stefan Kroiß |
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Institution: | Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, D-81377 München, Germany |
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Abstract: | The key reactions in the general synthesis of strobilurins are the highly (Z)-selective Wittig reaction of an (E)-cinnamaldehyde with the phosphorus ylide 8 derived from (1,1-dibromoethyl)triphenylphosphonium bromide, followed by bromine-iodine exchange and Pd-Cu co-catalyzed Stille cross-coupling of the resulting alkenyl iodide with methyl (Z)-2-tributylstannyl-3-methoxyacrylate (7). The synthetic strobilurins G, M, and N were identical with the corresponding natural compounds. In addition, the (2′ S)-configuration of strobilurin G (1) was unambiguously established by oxidative degradation of the synthetic intermediate (S)-9 to (R)-2,3-dihydroxyisovaleric acid. |
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Keywords: | Strobilurins Benzodioxepins Fungicides Natural products Total synthesis |
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