Intramolecular Diels-Alder reactions: Construction of aza- and diaza-steroid type skeletons

✍ Scribed by Heinz W. Gschwend

• Book ID: 102857592
• Publisher: John Wiley and Sons
• Year: 1973
• Tongue: German
• Weight: 869 KB
• Volume: 56
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19730560536

✦ Synopsis

Abstract

The preparation of 2‐(4‐phenyl)butadienyl‐piperidine 5 is described. An intramolecular Diels‐Alder reaction of the intermediately formed fumaramide thereof produces stereoselectively the tricyclic lactam 6. Its structure, as well as the configurational relationship of its 5 asymmetric centers, is corroborated on the basis of the NMR.‐data. Cycloacylation of the thermodynamically stable precursors 13 and 20 leads to pentacyclic aza‐ or diaza‐steroid type skeletons. Their structures (14, 16, and 21) and in particular their relative configurations are elaborated. A few qualitative kinetic aspects of this intramolecular (4+2)‐cycloaddition are presented.