vic-Iodo Thiocyanates and Iodo Isothiocyanates. IX. A Synthesis of Penam and Other Polycyclic Β-Lactams

RC Cambie, GR Clark, TC Jones, PS Rutledge…

Index: Cambie, Richard C.; Clark, George R.; Jones, Tony C.; Rutledge, Peter S.; Strange, Gary A.; Woodgate, Paul D. Australian Journal of Chemistry, 1985 , vol. 38, # 5 p. 745 - 764

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Citation Number: 11

Abstract

Abstract Penam (4-thia-1-azabicyclo [3.2. 0] heptan-7-one) and 2, 3-disubstituted penams are prepared conveniently from vic-iodo isothiocyanates beginning with the facile cyclization of the latter with di-t-butyl sodiomalonates. Treatment of the resulting di-t-butyl 2-(thiazolidin- 2-ylene) malonates with trifluoroacetic acid gives t-butyl 2-thiazolin-2-ylacetate derivatives which are reduced to the corresponding thiazolidines with aluminium amalgam. Cleavage ...