Hydroalumination of 3-butyn-1-ol: Application to a stereoselective synthesis of (3E,5Z)-3,5-dodecadienyl acetate, the sex pheromone of the leaf roller moth

Tetrahedron

Volumn 55, Issue 50, 1999, Pages 14243-14250

  Chong, J Michael ^a   Heuft, Matthew A ^a  

^a UNIVERSITY OF WATERLOO   (Canada)

Author keywords

Aluminium and compounds; Dienes; Pheromones

Indexed keywords

ACETIC ACID DERIVATIVE; ALUMINUM DERIVATIVE; SEX PHEROMONE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION KINETICS; LIQUID CHROMATOGRAPHY; MOTH; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0033544750     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00899-6     Document Type: Article

References (25)

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3. Well documented examples include disparlure (Cardé, R. T.; Doane, C. C.; Farnum, D. G. Environ. Entomol. 1978, 7, 815-816) and japonilure (Tumlinson, J. H.; Klein, M. G.; Doolittle, R. E.; Ladd, T. L.; Proveaux, A. T. Science 1977, 197, 789-792).
4. Well documented examples include disparlure (Cardé, R. T.; Doane, C. C.; Farnum, D. G. Environ. Entomol. 1978, 7, 815-816) and japonilure (Tumlinson, J. H.; Klein, M. G.; Doolittle, R. E.; Ladd, T. L.; Proveaux, A. T. Science 1977, 197, 789-792).
5. See, for example, serricornin (Levinson, H. Z.; Levinson, A. R. J. Appl. Entomol. 1987, 103, 217-240) and stegobinone (Kodama, H.; Ono, M.; Kohno, M.; Ohnishi, A. J. Chem. Ecol. 1987, 13, 1859).
6. See, for example, serricornin (Levinson, H. Z.; Levinson, A. R. J. Appl. Entomol. 1987, 103, 217-240) and stegobinone (Kodama, H.; Ono, M.; Kohno, M.; Ohnishi, A. J. Chem. Ecol. 1987, 13, 1859).
7. Adati, T.; Tatsuki, S. J. Chem. Ecol. 1999, 25, 105-115.
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10. For a review on the synthesis of insect pheromones, including conjugated dienes, see: Mori, K. In The Total Synthesis of Natural Products, Volume 9, ApSimon, J., Ed., John Wiley & Sons:Toronto, 1992, pp. 1- 534.
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14. Bis-hydroalumination is a common side reaction in the hydroalumination of alkynes: Zweifel, G.; Miller, J. A. Organic Reactions 1984, 32, 375-517. In our hands, hydroalumination/iodination of 1- octyne gave E-1-iodo-1-octene, 1-iodo-1-octyne, and 1-iodooctane in a ratio (GC) of 90:5:5.
15. Sih, C. J.; Salomon, R. G.; Proce, P.; Sood, R.; Peruzzotti, G. J. Am. Chem. Soc. 1975, 97, 857-865.
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19. Similarly, the difference in reactivity of E and Z vinylstannanes has been exploited to prepare pure E vinyllithiums by treating an isomeric mixtureof vinylstannanes with a limiting amount of alkyllithium: Pereyre, M.; Quintard, J.-P.; Rahm. Tin in Organic Synthesis, Butterworths: London, 1987, p. 155.
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21. A diyne alcohol (ca. 2%) was also detected by GC-MS but was readily removed by chromatography.
22. Samples of all four isomers of 3,5-dodecadienyl acetate were kindly provided by Professor Unelius, Royal Institute of Techonology, Stockholm. A 30 m x 0.25 mm DB-1701 column was used isothermally at 140 °C with He as the carrier gas. Retention times for the 3E,5Z; 3Z,5E; 3Z,5Z and 3E,5E isomers were 11.61, 11.79, 12.85, and 13.08 minutes, respectively.
23. For example, (3E,5Z)-3,5-tetradecadienyl acetate is a sex attractant of the white-barred groundling moth: Toth, M.; Doolittle, R. E. J. Chem. Ecol. 1992, 18, 1093-1105; (3E,5Z)-3,5-tetradecadienoic acid is a pheromone of the black carpet beetle: Tsuboi, S.; Masuda, T.; Takeda, A. Bull. Chem. Soc. Japan 1983, 56, 3521-3522.
24. For example, (3E,5Z)-3,5-tetradecadienyl acetate is a sex attractant of the white-barred groundlingmoth: Toth, M.; Doolittle, R. E. J. Chem. Ecol. 1992, 18, 1093-1105; (3E,5Z)-3,5-tetradecadienoic acid is a pheromone of the black carpet beetle: Tsuboi, S.; Masuda, T.; Takeda, A. Bull. Chem. Soc. Japan 1983, 56, 3521-3522.
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