An efficient approach to asymmetric synthesis of dipeptide β-turn mimetics: Indolizidinone amino acids

Wei Wang, Chiyi Xiong, Victor J. Hruby

Research output: Contribution to journalArticle

42 Scopus citations

Abstract

Azabicyclo[X.Y.0] alkane amino acids are rigid dipeptide β-turn mimetics with great potential applications for drug discovery. The lack of efficient methods to synthesize these compounds is a major bottleneck in this field. Herein we report an efficient approach to the enantiopure synthesis of (3S,6S,9S) and (3R,6R,9R) methyl 2-oxo-3-[N-(Boc/Cbz)amino]-1-azabicyclo[4.3.0]nonane-9-carboxylates 1. In this approach, the key intermediates 5a and 5b with different stereochemical configurations were efficiently constructed from the same precursor in high stereoselectivity via asymmetric hydrogenations using (S,S) or (R,R) Et-DUPHOS, Rh(I)-based catalysts. The process, starting from inexpensive diethyl 1,3-acetonedicarboxylate 2, can allow for the practical synthesis of this class of compounds.

Original languageEnglish (US)
Pages (from-to)3159-3161
Number of pages3
JournalTetrahedron Letters
Volume42
Issue number18
DOIs
StatePublished - Apr 30 2001

Keywords

  • Amino acids
  • Asymmetric hydrogenation
  • β-turn mimetics

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'An efficient approach to asymmetric synthesis of dipeptide β-turn mimetics: Indolizidinone amino acids'. Together they form a unique fingerprint.

  • Cite this