A substituted hydropyrazino[1,2-a]pyrimidin-6-one derivative was synthesized stereoselectively via the intramolecular N-acyliminium ion cyclization between an amide nitrogen and an Nα-acetal derived from Cbz-protected aminopropyl-phenylalaninamide in very good yields. The formation of a single diastereomer is due to the low energy chairlike conformation of its bicyclic structure. This methodology provides a convenient tool to build internal bicyclic peptidomimetics.
- Internal bicyclic peptidomimetics
- N-Acylimnium ion cyclization
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry
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Min, B. J. (Creator), Gu, X. (Creator), Yamamoto, T. (Creator), Petrov, R. R. (Creator), Qu, H. (Creator), Lee, Y. S. (Creator) & Hruby, V. J. (Creator), Cambridge Crystallographic Data Centre, 2008