Solid-phase synthesis and stereochemical assignments of tenuecyclamides A-D employing heterocyclic amino acids derived from commercially available Fmoc alpha-amino acids

Academic Article
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related to degree

  • Deechongkit, Songpon, Ph.D. in Organic Chemistry, Scripps Research 1999 - 2003

publication date

  • 2004

abstract

  • [reaction: see text] The solid-phase assembly of heterocyclic amino acids enabled the total synthesis of numerous diastereoisomers of tenuecyclamides A-D, establishing or correcting the stereochemistry of each natural product. This strategy provides a very efficient route to synthesize thiazole- and oxazole-containing macrolactams from heterocyclic amino acids that are readily prepared from Fmoc-alpha-amino acids. This methodology appears to be broadly applicable to the synthesis of natural product libraries incorporating unnatural heterocyclic amino acid residues for the purpose of drug discovery.