Solid-phase synthesis and stereochemical assignments of tenuecyclamides A-D employing heterocyclic amino acids derived from commercially available Fmoc alpha-amino acids.
[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.
You
Shu-Li
SL
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, La Jolla, California 92037, USA.
Deechongkit
Songpon
S
Kelly
Jeffery W
JW
D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013844:Thiazoles / Q000138:chemical synthesis* / Q000737:chemistry*
D000596:Amino Acids; D007202:Indicators and Reagents; D010456:Peptides, Cyclic; D013844:Thiazoles; C495939:tenuecyclamide A; C495940:tenuecyclamide C; C495941:tenuecyclamide D