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Issue 0, 1985
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Use of π-allyltricarbonyliron lactam complexes in the preparation of nocardicin derivatives: synthesis of (–)-3-oxo-1-[(p-benzyloxyphenyl)-benzyloxycarbonylmethyl]azetidin-2-one

Abstract

A short five-step synthesis, in 79% overall yield, of (–)-3-Oxo-1 -[(p-benzyloxyphenyl) benzyloxy-carbonylmethyl]azetidin-2-one (3), a precursor for nocardicin synthesis has been developed from isoprene monoepoxide. The key steps of the procedure rely on the efficient transformation of 2–4-η3-(1-formyloxy-2-methylbut-3-en-2-ylato)tricarbonyliron into the corresponding diastereoisomeric lactam complexes (6) and (7) using D-(–)-benzyl-(p-benzyloxyphenyl)glycinate (5) and ZnCl2·TMEDA (TMEDA = tetramethylethylenediamine), and their oxidation with ceric ammonium nitrate to 3-isopropenylazetidinone derivatives.

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Article type: Paper
DOI: 10.1039/P19850002375
Citation: J. Chem. Soc., Perkin Trans. 1, 1985,0, 2375-2381

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    Use of π-allyltricarbonyliron lactam complexes in the preparation of nocardicin derivatives: synthesis of (–)-3-oxo-1-[(p-benzyloxyphenyl)-benzyloxycarbonylmethyl]azetidin-2-one

    S. T. Hodgson, D. M. Hollinshead, S. V. Ley, C. M. R. Low and D. J. Williams, J. Chem. Soc., Perkin Trans. 1, 1985, 0, 2375
    DOI: 10.1039/P19850002375

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