TY - JOUR
T1 - Synthesis of hydroxy-substituted unsaturated fatty acids and the amino-acid insect-derivative volicitin
AU - Wei, Han Xun
AU - Truitt, Christopher L.
AU - Paré, Paul W.
N1 - Funding Information:
We thank D. Purkiss for expert NMR support. NMR instrumentation was purchased by NSF (CHE-9808436); project financial support was provided by NRI/USDA (grant #35320-9378) and The Herman Frasch Foundation for Chemical Research.
PY - 2003/1/20
Y1 - 2003/1/20
N2 - An efficient synthesis of N-(17S-hydroxylinolenoyl)-L-glutamine (volicitin), a chemical elicitor from the herbivore-pest beet armyworm is presented. The synthesis, which utilizes a copper-catalyzed acetylene coupling, links (S)-3,6-heptadiyne-2-ol with a C-8 propargylic iodine methyl ester to form the (S)-17-hydroxylinolenate skeleton. By substituting different heptadiyne-2-ol groups, a series of methylene interrupted polyacetylene analogues were generated.
AB - An efficient synthesis of N-(17S-hydroxylinolenoyl)-L-glutamine (volicitin), a chemical elicitor from the herbivore-pest beet armyworm is presented. The synthesis, which utilizes a copper-catalyzed acetylene coupling, links (S)-3,6-heptadiyne-2-ol with a C-8 propargylic iodine methyl ester to form the (S)-17-hydroxylinolenate skeleton. By substituting different heptadiyne-2-ol groups, a series of methylene interrupted polyacetylene analogues were generated.
UR - http://www.scopus.com/inward/record.url?scp=0037455087&partnerID=8YFLogxK
U2 - 10.1016/S0040-4039(02)02640-0
DO - 10.1016/S0040-4039(02)02640-0
M3 - Article
AN - SCOPUS:0037455087
VL - 44
SP - 831
EP - 833
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 4
ER -