
TY  - JOUR
A1  - Balgir, BS 
A1  - Mander, LN 
A1  - Prager, RH 
T1  - Studies on intramolecular alkylation. III. The preparation of &#947;-lactams from podocarpic acid: Models for diterpene alkaloid synthesis
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1974
VL  - 27
IS  - 6
SP  - 1245
EP  - 1256
KW  - 
UR  - https://doi.org/10.1071/CH9741245 
N2  - 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). 
ER  -

