An improved and efficient copper (I) mediated coupling procedure was used to synthesize N-(17-hydroxylinolenoyl)-L-glutamine (volicitin), a chemical elicitor from the herbivore pest beet army worm, and its biologically active analogs.
(a) AlbornHT, TurlingsTCJ, JonesTH, StenhagenG, LoughrinJH, TumlinsonJH. (1997) An elicitor of plant volatiles from beet armyworm oral secretion. Science, 276, 945–949
3.
(b) PohnertG, JungV, HaukiojaE, LempaK, BolandW. (1999) New fatty acid amides from regurgitant of Lepidopteran (Noctuidae, Geometridae) caterpillars. Tetrahedron, 55, 11275–11280
4.
(c) HalitschkeR, SchittkoU, PohnertG, BolandW, BaldwinIT. (2001) Molecular interactions between the specialist herbivore Manduca sexta (Lepidoptera, Sphingidae) and its natural host Nicotiana attenuata. III. Fatty acid-amino acid conjugates in herbivore oral secretions are necessary and sufficient for herbivore-specific plant responses. Plant Physiology, 125, 711–717.
5.
ParéPW, AlbornHT, TumlinsonJH. (1998) Concerted biosynthesis of an insect elicitor of plant volatiles. Proceedings of National Academy of Sciences USA, 95, 13971–13975.
6.
TruittCL, ParéPW. (2004) In situ translocation of volicitin by beet armyworm larvae to maize and systemic immobility of the herbivore elicitor in plants. Planta, 218, 999–1007.
7.
TruittCL, WeiHX, ParéPW. (2004) A plasma membrane protein from Zea mays binds with the herbivore elicitor volicitin. Plant Cell, 16, 523–532.
8.
(a) PohnertG, KochT, BolandW. (1999) Synthesis of volicitin: a novel three-component Wittig approach to chiral 17-hydroxylinolenic acid. Chemical Communications, 1087–1088
9.
(b) AlbornHT, JonesTH, StenhagenGS, TumlinsonJH. (2000) Identification and synthesis of volicitin and related components from beet armyworm oral secretions. Journal of Chemical Ecology, 26, 203–220
10.
(c) HansenTV, StenstrømY. (2000) A facile formal synthesis of volicitin. Synthetic Communications, 30, 2549–2557
11.
(d) ItohS, KuwaharaS, HasegawaM, KodamaO. (2002) Synthesis of the (17R)- and (17S)-isomers of volicitin, an elicitor of plant volatiles contained in the oral secretions of the beet armyworm. Bioscience, Biotechnology and Biochemistry, 66, 1591–1596.
12.
WeiHX, TruittCL, ParéPW. (2003) Synthesis of hydroxy-substituted unsaturated fatty acids and the amino-acid insect-derivative volicitin. Tetrahedron Letters, 44, 831–833.
13.
MoriK, EbataT. (1986) Synthesis of optically active pheromones with an epoxy ring, (+)-disparlure and both the enantiomers of (3Z,6Z)-cis-9,10-epoxy-3,6-heneicosadiene. Tetrahedron, 42, 3471–3478.
14.
RamaRao AV, ReddyER. (1986) Stereoselective synthesis of hydroxy octadecatrienoic acids, the self defensive substances in rice plant. Tetrahedron Letters, 27, 2279–2282.
(a) MitsunobuO. (1981) The use of dethyl azodicarboxylate and triphenylphosphine in synthesis and transformation of natural products. Synthesis, 1–28
17.
(b) LalB, PramanikBN, ManhasMS, BoseAK. (1977) Diphenylphosphoryl azide, a novel reagent for the stereospecific synthesis of azides from alcohols. Tetrahedron Letters, 23, 1977–1980.
18.
DuffyMG, GraysonDH. (2002) Conversion of (Z)-1,4-dihydroxyalk-2-enes into 2,5-dihydrofurans and of alkane-1,4-diols into tetrahydrofurans via acid-catalysed cyclisation of the monoisoureas formed by their copper(I)-mediated reactions with dicyclohexylcarbodiimide. Journal of Chemical Society, Perkin Transactions I, 1555–1563.
19.
BerréeF, MichelotG, Le CorreM. (1998) N-Boc ethyl oxamate: a new nitrogen nucleophile for use in Mitsunobu reactions. Tetrahedron Letters, 39, 8275–8276.
20.
BrownCA, AhujaVK. (1973) Catalytic hydrogenation. VI. The reaction of sodium borohydride with nickel salts in ethanol solution. P-2 nickel, a highly convenient, new, selective hydrogenation catalyst with great sensitivity to substrate structure. Journal of Organic Chemistry, 38, 2226–2232.
21.
FaragMA, FokarM, AbdH, ZhangH, AllenRD, ParéPW. (2005) (Z)-3-Hexenol induces defense genes and down-stream metabolites in maize. Planta, 220, 900–909.
