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A second-generation synthesis of scalemic 3,5,5-trisubstituted pyrrolin-4-ones: Incorporation of functionalized amino acid side-chains

✍ Scribed by Amos B. Smith III; Andrew B. Benowitz; David A. Favor; Paul A. Sprengeler; Ralph Hirschmann

Book ID: 104257114
Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 283 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)00752-1

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✦ Synopsis

To access mimics of peptidal ~-strands (1), scalemic 3,5,5-trisubstituted pyrrolin-4-ones bearing the tyrosine, serine, and lysine side-chains have been generated via cyclization of metalated imino esters and deprotection. The functionalized imino esters were prepared by asymmetric alkylation of a common oxazolidinone precursor (2) derived from Lprenylglycine.

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