
%0 Journal Article
%A Balgir, BS 
%A Mander, LN 
%A Prager, RH 
%T Studies on intramolecular alkylation. III. The preparation of &#947;-lactams from podocarpic acid: Models for diterpene alkaloid synthesis
%J Australian Journal of Chemistry
%D 1974/06/01
%V 27
%N 6
%P 1245-1256
%K 
%R https://doi.org/10.1071/CH9741245
%U https://www.publish.csiro.au/paper/CH9741245 
%X Several methods for the introduction of a 6&#946;,16 nitrogen bridge in podocarpane derivatives are described. Attempted intramolecular N-alkylation in the 6&#945;-bromo amide (9) gave ketol (13) via imino ether (10). Attempted lactam formation from the 6-oxo nitrile (22) or 6-oxo ester (24) gave no useful result, but the diosphenol(15) gave lactam (16), which was reduced to the target lactam (28).  A further route to (28) via the 6-ene derivative of amide (7) is also described. The lack of identity between (28) and the &#947;-lactam formed from photolysis of O-methylpodocarpoyl azide indicated that this lactam has the 2&#946;,19 structure (31). 
