The synthesis of bicyclic lactam based His-Pro building blocks: The effect of substituent polarity on an intramolecular bond migration

Wenhua Chu, Kevin D. Moeller

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

A strategy for constructing bicyclic lactam amino acid building blocks with imidazole sidechains is reported. The synthetic route described utilizes an electrochemical amide oxidation to functionalize a proline derivative, and then a sequential cyclization-rearrangement strategy to construct a substituted six-membered ring lactam. Alternatively, the seven-membered ring lactams were obtained without rearrangement when electron withdrawing groups were present beta to the amide carbonyl.

Original languageEnglish
Pages (from-to)7939-7943
Number of pages5
JournalTetrahedron Letters
Volume40
Issue number45
DOIs
StatePublished - Nov 5 1999

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