Advanced search
Publication Cover
Bioscience, Biotechnology, and Biochemistry Volume 66, 2002 - Issue 7
Journal homepage
258
Views
12
CrossRef citations to date
0
Altmetric
Original Articles

Synthesis of the (17R)- and (17S)-Isomers of Volicitin, an Elicitor of Plant Volatiles Contained in the Oral Secretion of the Beet Armyworm

Seiji ITOHLaboratory of Agricultural Chemicals, Faculty of Agriculture, Ibaraki University Ami-machi, Inashiki-gun, Ibaraki 300-0393, Japan;Laboratory of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan
,
Shigefumi KUWAHARALaboratory of Applied Bioorganic Chemistry, Division of Life Science, Graduate School of Agricultural Science, Tohoku University 1-1 Tsutsumidori-Amamiyamachi, Aoba-ku, Sendai 981-8555, Japan
,
Morifumi HASEGAWALaboratory of Agricultural Chemicals, Faculty of Agriculture, Ibaraki University Ami-machi, Inashiki-gun, Ibaraki 300-0393, Japan
&
Osamu KODAMALaboratory of Agricultural Chemicals, Faculty of Agriculture, Ibaraki University Ami-machi, Inashiki-gun, Ibaraki 300-0393, Japan
Pages 1591-1596 | Received 23 Jan 2002, Accepted 18 Feb 2002, Published online: 22 May 2014

  • 1) Alborn, H. T., Turlings, T. C. J., Jones, T. H., Stenhagen, G., Loughrin, J. H., and Tumlinson, J. H., An elicitor of plant volatiles from beet armyworm oral secretion. Science, 276, 945-959 (1997).
  • 2) Alborn, H. T., Jones, T. H., Stnhagen, G. S., and Tumlinson, J. H., Identification and synthesis of volicitin and related compounds from beet armyworm oral secretions. J. Chem. Ecol., 26, 203-220 (2000).
  • 3) Pohnert, G., Koch, T., and Boland, W., Synthesis of volicitin: a novel three-component Wittig approach to chiral 17-hydroxylinolenic acid. Chem. Commun., 1087-1088 (1999).
  • 4) Pohnert, G. and Boland, W., Highly efficient one-pot double-Michael approach to unsymmetrical (1Z,4Z,7Z)-homoconjugated trienes. Eur. J. Org. Chem., 1821-1826 (2000).
  • 5) Spiteller, D., Pohnert, G., and Boland, W., Absolute configuration of volicitin, an elicitor of plant volatile biosynthesis from lepidopteran larvae. Tetrahedron Lett., 42, 1483-1485 (2001).
  • 6) Hansen, T. V., and Stenstrøm, Y., A facile formal synthesis of volicitin. Synth. Commun., 30, 2549-2557 (2000).
  • 7) Blanchette, M. A., Malamas, M. S., Nantz, M. H., Roberts, J. C., Somfai, P., Whritenour, D. C., and Masamune, S., Synthesis of bryostatins. 1. Construction of the C(1)-C(16) fragment. J. Org. Chem., 54, 2817-2825 (1989).
  • 8) Tanaka, A. and Oritani, T., A mild and efficient method for converting alcohols and tetrahydropyranyl ethers to bomides with inversion of configuration. Tetrahedron Lett., 38, 1955-1956 (1997).
  • 9) Kuwahara, S., Tsuruta, T., Leal, W. S., and Kodama, O., Synthesis of both the enantiomers of 15-hexadecanolide, a sex pheromone component of the stink bug, Piezodorus hybneri. Biosci. Biotechnol. Biochem., 62, 1261-1263 (1998).
  • 10) Massad, S. K., Hawkins, L. D., and Baker, D. C., A series of (2S)-2-O-protected-2-hydroxypropanal (L-lactaldehydes) suitable for use as optically active intermediate. J. Org. Chem., 48, 5180 (1983).
  • 11) Marshall, J. A. and Xie, S., Synthesis of a C22-34 subunit of the immunosuppressant FK-506. J. Org. Chem., 60, 7230-7237 (1995).

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.