Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues?

Organic & Biomolecular Chemistry Pub Date: 2003-06-05 DOI: 10.1039/B303924B

Abstract

Alkylation reactions using α-halolactams or lactam enolates derived from bicyclic lactam templates can proceed with high endo- or exo- diastereoselectivity respectively. In the latter case, stereochemical correction by means of enolate generation and hindered phenol quench is possible with moderate efficiency. This protocol has been applied to the synthesis of protected penmacric acid and its analogues.

Graphical abstract: Pyrrolidinones derived from (S)-pyroglutamic acid: penmacric acid and analogues
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