Tetrahedron

Synthesis of the β-lactam antibiotic (+)-thienamycin via an intermediate π-allyltricarbonyliron lactone complex

ST Hodgson, DM Hollinshead, SV Ley

Index: Hodgson, Simon T.; Hollinshead, David M.; Ley, Steven V. Tetrahedron, 1985 , vol. 41, # 24 p. 5871 - 5878

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Citation Number: 34

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 ...

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