Synthesis of the β-lactam antibiotic (+)- thienamycin via an intermediate π-allyltricarbonyliron lactone complex |
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Authors: | Simon T Hodgson David M Hollinshead Steven V Ley |
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Institution: | Department of Chemistry, Imperial College, London SW7 2AY, U.K. |
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Abstract: | The π-allyltricarbonyliron lactone complex (7), formed by reaction of E-1,2-epoxy-2-methyl-6,6-dimethoxyhex-3-ene(5) with co-ordinatively unsaturated iron carbonyl species, was reacted with benzylamine to give a lactam complex (8) by an SN'-like mechanism. This complex upon oxidation with Ce(IV) afforded cis-3-isopropenyl-4-(2',2'-dim (9) which was chemically modified into trans-3-(1'-hydroxyethyl)-4-(2',2-dimethoxy)ethyl] azetidin-2-one (13), a key intermediate previously used in the synthesis of the antibiotic thienamycin. Similar reaction with (S)-(-)- -methylbenzylamine afforded a separable mixture of diastereoisomeric iron lactam complexes (16 and 17). These complexes could be individually converted to the corresponding optically active β-lactam derivatives (27 and 28) and, hence, are precursors for the synthesis of either natural (+)-thienamycin or unnatural (-)-thienamycin. |
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