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Die chemoenzymatische Synthese von Tetrodotoxin, die T. Hudlicky et al. in ihrer Zuschrift auf S. 11160 ff. beschreiben, beinhaltet eine regio‐ und enantioselektive Dihydroxylierung von Benzylacetat durch einen rekombinanten Organismus, E. coli JM109 (pDTG601A), der eine Toluoldioxygenase überexprimiert. Das entstehende homochirale Diendiol ist eine ideale Ausgangsverbindung für die enantioselektive...
Advanced intermediates for the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps include the toluene dioxygenase mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed into Fukuyama's intermediate in six steps, into Alonso's intermediate in nine steps, and into Sato's intermediate in ten steps.
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