Mixed metal base LICKOR as key reagent in the synthesis of conjugate alkadien-1-ols. A new route to an insect attractant

Tetrahedron

Volumn 54, Issue 48, 1998, Pages 14603-14608

  Cominetti, Fulvio ^a   Deagostino, Annamaria ^a   Prandi, Cristina ^a   Venturello, Paolo ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMOATTRACTANT;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; FLY; INSECT; NONHUMAN; PRIORITY JOURNAL; SYNTHESIS;

EID: 0032569788     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00918-1     Document Type: Article

References (32)

1. 1. Partly taken from Laurea Thesis of F. C.
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3. 2. Schlosser, M. J. Organomet. Chem., 1967, 8, 9-16. For reviews see: Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271. A. Mordini, Advances in Carbanion Chemistry, V. Snieckus, Ed.; JAI Press Inc.: Greenwich CT, 1992; Vol 1, p 1-44. Schlosser, M.; Faigl, F.; Franzini, L.; Geneste, H.; Katsoulos, G.; Zhong, G. Pure Appl. Chem., 1994, 66, 1439-1446.
4. 2. Schlosser, M. J. Organomet. Chem., 1967, 8, 9-16. For reviews see: Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271. A. Mordini, Advances in Carbanion Chemistry, V. Snieckus, Ed.; JAI Press Inc.: Greenwich CT, 1992; Vol 1, p 1-44. Schlosser, M.; Faigl, F.; Franzini, L.; Geneste, H.; Katsoulos, G.; Zhong, G. Pure Appl. Chem., 1994, 66, 1439-1446.
5. 2. Schlosser, M. J. Organomet. Chem., 1967, 8, 9-16. For reviews see: Schlosser, M. Mod. Synth. Methods 1992, 6, 227-271. A. Mordini, Advances in Carbanion Chemistry, V. Snieckus, Ed.; JAI Press Inc.: Greenwich CT, 1992; Vol 1, p 1-44. Schlosser, M.; Faigl, F.; Franzini, L.; Geneste, H.; Katsoulos, G.; Zhong, G. Pure Appl. Chem., 1994, 66, 1439-1446.
6. 3. Mordini, A.; Ben Rayana, E.; Margot, C.; Schlosser, M. Tetrahedron, 1990, 46, 2401-2410.
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9. 5. Venturello, P. J. Chem. Soc., Chem. Commun. 1992, 1032-1033. Prandi, C; Venturello, P. J. Org. Chem., 1994, 59, 5458-5462. Deagostino, A.; Prandi, C; Venturello, P. Tetrahedron, 1996, 52, 1433-1442, and references therein.
10. 5. Venturello, P. J. Chem. Soc., Chem. Commun. 1992, 1032-1033. Prandi, C; Venturello, P. J. Org. Chem., 1994, 59, 5458-5462. Deagostino, A.; Prandi, C; Venturello, P. Tetrahedron, 1996, 52, 1433-1442, and references therein.
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12. (b) Deagostino, A.; Maddaluno, J.; Mella, M.; Prandi, C; Venturello, P. J. Chem. Soc., Perkin Trans. l 1998, 881-888.
13. 7. (4E,7E)nona-4,7-dien-1-ol has been used in the synthesis of the terpenoid metabolite cerutenin, see: Boeckmann, R. K. Jr.; Thomas, E. W. J. Am. Chem. Soc. 1979, 101, 987-994. (11E,13E)pentadeca-11,13-dien-1-ol was a precursor of cytochalasin B, see: Bailey, S. Y.; Thomas, E. J.; Turner, W. B. J. Chem. Soc., Chem. Commun. 1978, 474-475.
14. 7. (4E,7E)nona-4,7-dien-1-ol has been used in the synthesis of the terpenoid metabolite cerutenin, see: Boeckmann, R. K. Jr.; Thomas, E. W. J. Am. Chem. Soc. 1979, 101, 987-994. (11E,13E)pentadeca-11,13-dien-1-ol was a precursor of cytochalasin B, see: Bailey, S. Y.; Thomas, E. J.; Turner, W. B. J. Chem. Soc., Chem. Commun. 1978, 474-475.
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22. f, both by GC and TLC analyses. We have not carefully examined the configuration of compounds 2 and 3, since the observed selectivity might be of some interest, but it is unimportant in the present case. In the following step of the synthesis the 1,4-elimination process induces the C-C double bond shift.
23. 14. Two isomers have been detected (by GC-MS analysis) in the reaction mixture, and only the major one (≥ 98%) has been characterized as the (4E,6E) isomer (see Experimental Part). This result appears to be in contrast with what we reported in ref. 6(b), concerning the 1,4-elimination reaction carried out on 2-(but-1-enyl)-1,3-dioxane: in that case the E,Z isomer predominated. Experiments are in progress to account for these opposite outcomes.
24. 15. For analogous cases proving the different reactivity of Schlossers bases and alkyllithium reagents, compare for example the results reported by Bailey, W. F.; Zartun, D. L. J. Chem Soc., Chem. Commun. 1984, 34-35 and by Mioskowski, C., Manna, S.; Falck, J. R. Tetrahedron Lett. 1984, 25, 519-522 with those of ref. 5.
25. 15. For analogous cases proving the different reactivity of Schlossers bases and alkyllithium reagents, compare for example the results reported by Bailey, W. F.; Zartun, D. L. J. Chem Soc., Chem. Commun. 1984, 34-35 and by Mioskowski, C., Manna, S.; Falck, J. R. Tetrahedron Lett. 1984, 25, 519-522 with those of ref. 5.
26. 16. Margot, C; Matsuda, H.; Schlosser, M. Tetrahedron 1990, 46, 2425-2430.
27. 17. Schtenk, W.; Bergmann, E., Liebigs Ann. Chem. 1928, 464, 1-42.
28. 18. Longer reaction time, or insufficient cooling, causes formation of the corresponding dimeric ester as a by-product, and reduces reaction yield. For analogous cases of dimeric by-products, see ref. 10. Some preliminary tests, indicate moreover that it is important to activate molecular sieves (T = 150 °C, pressure = 10 mmHg), in order to improve the yield of the oxidation reaction.
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