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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Studies on intramolecular alkylation. III. The preparation of γ-lactams from podocarpic acid: Models for diterpene alkaloid synthesis

BS Balgir, LN Mander and RH Prager

Australian Journal of Chemistry 27(6) 1245 - 1256
Published: 1974

Abstract

Several methods for the introduction of a 6β,16 nitrogen bridge in podocarpane derivatives are described. Attempted intramolecular N-alkylation in the 6α-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 γ-lactam formed from photolysis of O-methylpodocarpoyl azide indicated that this lactam has the 2β,19 structure (31).

https://doi.org/10.1071/CH9741245

© CSIRO 1974

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