Total synthesis and structural revision of the cytotoxin aruncin B
The sodium salts E-15 and Z-15 of the originally proposed dihydropyran acid structure of aruncin B (1) were prepared through RCM and ethoxyselenation−selenoxide elimination, but acid sensitivity of these salts, together with inconsistencies in the spectral data suggested a significant structural mis...
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| Format: | Journal article |
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American Chemical Society
2016
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| Summary: | The sodium salts E-15 and Z-15 of the originally proposed dihydropyran acid structure of aruncin B (1) were prepared through RCM and ethoxyselenation−selenoxide elimination, but acid sensitivity of these salts, together with inconsistencies in the spectral data suggested a significant structural misassignment. A β-iodo Morita-Baylis-Hillman reaction to give Z-iodo ester 24, followed by Sonogashira cross-coupling−5-exo-dig lactonization provided concise access to a Z-γ-alkylidenebutenolide 18, which possessed data corresponding to that originally reported for aruncin B. |
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