Pheromones are chemicals that are secreted by insects to communicate location of food sources, presence of danger, and to attract mates. One of the pheromones secreted by cone beetles (Conophthorus banksianae, C.resinosae, and C. coniperda) is trans-conophthorin.
The goal of this project is to synthesize this natural pheromone from readily available starting materials so that it can be used in biological studies with cone beetles.
We developed a six-step synthesis that would start with materials we could purchase inexpensively, and would hopefully end at our target compound,
trans-conophthorin.
After each step in the synthesis, we characterized the intermediate products using one or more of the following techniques: thin-layer chromatography, IR spectroscopy,
GC-MS, and
NMR. We have successfully completed all steps in the synthesis, except the last one. The NMR spectrum of the second to the last product summarizes our success up to this point.
Dr. Dan Blanchard
Synthesis of a Known Insect Pheromone: trans-Conophthorin
Robert Hachtman, Jaclyn Berg, Christopher DiJiacomo, and Dr. Dan Blanchard
| (5R,7S)-7-Methyl-1,6-dioxaspiro[4.5]decane |
| Formula: | C9H16O2 |
| |
| MW: | 156.22 |
Reference(s) for synthesis of (5R,7S)-7-Methyl-1,6-dioxaspiro[4.5]decane
Fletcher, M.T., Wells, J.A., Jacobs, M.F., Krohn, S., Kitching, W., Drew, R.A.I., Moore, C.J., and Francke, W. 1992. Chemistry of fruit-flies. Spiroacetal-rich secretions in several Bactrocera species from the South-West Pacific region. J. Chem. Soc. Perkin Trans. 1:2827-2832.
2.23. 2-Methyl-1,6-dioxaspiro[4.5]decane (32)
The spiroketal 2-methyl-1,6-dioxaspiro[4.5]decane (32)was identified by Francke et al.112,113 as a minor pheromone component of the common wasp, Paravespula vulgaris. Zarbin et al.114 described a diastereoselective approach to (2R,5S)- and (2S,5R)-32. The route employed an alkylation reaction between the cyclopentanone N,N-dimethylhydrazone and the chiral iodides (R)- or (S)-A, controlling the stereocenter at C-2 of the molecules. The alkylated products were transformed into the 1,8-O-TBS-1,8-dihydroxy-5-nonanones in four steps, and a subsequent stereoselective spiroketalization in acidic media, afforded a diastereoisomeric mixture (1:2) of both isomers of 32 (Scheme 33).
http://www.scielo.br/scielo.php?pid=S0103-50532007000600003&script=sci_arttext
|
Dan Blanchard
Office Location: Boehm 312
Phone number: 610-683-1549
Fax Number: 610-683-1352
presentation
Publications
K. A. Mowery, D. E. Blanchard, S. Smith, T. A. Betts, “Investigation of Imposter Perfumes using GC-MS”, Journal of Chemical Education; 2004, 81; 87-89.
D.E. Blanchard, “Quantitative Microscale Hydrogenation of Vegetable Oils”, Journal of Chemical Education; 2003, 80; 544-546.
Z. Zhang, D. Li, D. E. Blanchard, S. R. Lear, S. K. Erickson, T.A. Spencer, “Key Regulatory Oxysterols in Liver: Analysis as Delta4-3-ketone Derivatives by HPLC and Response to Physiological Perturbations”, Journal of Lipid Research; 2001, 42; 649-658.
T. A. Spencer, T. J. Onofrey, R. O. Cann, J. S. Russel, L. E. Lee D. E. Blanchard,A. Castro, P. Gu, G. Jiang, I. Schechter, "Zwitterionic Sulfobetaine Inhibitors of Squalene Synthase",Journal of Organic Chemistry; 1999, 64(3); 807-818.
J.M. Lehmann, S.A. Kliewer, L.B. Moore, T.A. Smith-Ollver, B.B. Ollver, J.L. Su, S.S. Sundseth, D.A. Winegar, D.E. Blanchard, T.A. Spencer, T.M. Wilson, "Activation of the Nuclear Receptor LXR by Oxysterols Defines a New Hormone Response Pathway" The Journal of Biological Chemistry 1997, 272, 3137-3140.
D.S. Kemp, J.H. Rothman, T.P. Curran, D.E. Blanchard, "A Macrocyclic Triproline-Derived Template for Helix Nucleation" Tet. Letters 1995, 36, 3809-3812.
D.S. Kemp, D.E. Blanchard, C.C. Muendel, "Studies on the Nucleation in DMSO and Water of Beta Sheet Structures with Peptide-Epindolidione Conjugates" in Peptides: Chemistry, Structure, and Biology: Proceedings of Twelfth American Peptide Symposium, June 16-20, 1991, Cambridge, MA, USA; Smith, J.A. ed.; ESCOM: Leiden, 1992, pp. 319-322.
D.S. Kemp, D.E. Blanchard, C.C. Muendel, B.R. Bowen, "Diacylaminoepindolidiones as Models for Beta Sheet Structure" in Peptides: Chemistry, Structure, and Biology: Proceedings of the Eleventh American Peptide Symposium, July 9-14, 1989, La Jolla, CA, USA; Rivier, J.E. and Marshall, G.R., eds.; ESCOM: Leiden, 1990, p. 674.
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