Stereoselective bromination - Suzuki cross-coupling of dehydroamino acids to form novel reverse-turn peptidomimetics

Substituted unsaturated and saturated indolizidinone amino acids

Junyi Zhang, Chiyi Xiong, Wei Wang, Jinfa Ying, Victor J Hruby

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

(matrix presented) A general and efficient methodology has been developed to prepare the C4-substituted dipeptide reverse-turn mimetics unsaturated (9a, 10a) and saturated (11a) azabicyclo[4.3.0] alkane amino acid derivatives. The side chain was introduced by bromination of dehydroamino acid intermediates followed by Suzuki coupling. Hydrogenation of the bicyclic dehydroamino acid 9a afforded saturated bicyclic lactam 11a. This approach can be further explored for the synthesis of a variety of such β-turn mimetics with aryl and alkyl side chain functionalities.

Original languageEnglish (US)
Pages (from-to)4029-4032
Number of pages4
JournalOrganic Letters
Volume4
Issue number23
DOIs
StatePublished - Nov 14 2002

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Peptidomimetics
bromination
Halogenation
cross coupling
amino acids
Amino Acids
Lactams
acids
Alkanes
Acids
Hydrogenation
Dipeptides
alkanes
hydrogenation
methodology
Derivatives
synthesis
matrices

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Stereoselective bromination - Suzuki cross-coupling of dehydroamino acids to form novel reverse-turn peptidomimetics : Substituted unsaturated and saturated indolizidinone amino acids. / Zhang, Junyi; Xiong, Chiyi; Wang, Wei; Ying, Jinfa; Hruby, Victor J.

In: Organic Letters, Vol. 4, No. 23, 14.11.2002, p. 4029-4032.

Research output: Contribution to journalArticle

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