
TY  - JOUR
A1  - Cambie, RC 
A1  - Clark, GR 
A1  - Jones, TC 
A1  - Rutledge, PS 
A1  - Strange, GA 
A1  - Woodgate, PD 
T1  - <i>vic</i>-Iodo Thiocyanates and Iodo Isothiocyanates. IX. A Synthesis of Penam and Other Polycyclic &#914;-Lactams
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1985
VL  - 38
IS  - 5
SP  - 745
EP  - 764
KW  - 
UR  - https://doi.org/10.1071/CH9850745 
N2  - 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. 
ER  -

