
%0 Journal Article
%A Cambie, RC 
%A Clark, GR 
%A Jones, TC 
%A Rutledge, PS 
%A Strange, GA 
%A Woodgate, PD 
%T <i>vic</i>-Iodo Thiocyanates and Iodo Isothiocyanates. IX. A Synthesis of Penam and Other Polycyclic &#914;-Lactams
%J Australian Journal of Chemistry
%D 1985/05/01
%V 38
%N 5
%P 745-764
%K 
%R https://doi.org/10.1071/CH9850745
%U https://www.publish.csiro.au/paper/CH9850745 
%X 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 of these t-butyl esters with hydrogen chloride affords &#946;-amino acid hydrochlorides, which are cyclized to penam and its derivatives with 1-[3-( dimethylamino ) propyl ]- 3-ethylcarbodiimide hydrochloride. The structures of the (2&#945;,3a&#946;,7a&#946;)- thiazolidine  (5) and of the tricyclic &#946;- lactam (41) have been confirmed by X-ray crystallography. 
