Pheromone synthesis. Part 240: Cross-metathesis with Grubbs I (but not Grubbs II) catalyst for the synthesis of (R)-trogodermal (14-methyl-8-hexadecenal) to study the optical rotatory powers of compounds with a terminal sec-butyl group

Tetrahedron

Volumn 65, Issue 19, 2009, Pages 3900-3909

  Mori, Kenji ^a  

^a TOYO GOSEI CO LTD   (Japan)

Author keywords

Cross metathesis; Optical rotation; Pheromone; Trogodermal

Indexed keywords

8 NONENYL ACETATE; ACETIC ACID DERIVATIVE; ALKENE; CARBON; SEX PHEROMONE; TROGODERMAL (14 METHYL 8 HEXADECENAL); UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMER; OPTICAL ROTATION; PEST INSECT; PRIORITY JOURNAL; SYNTHESIS; TROGODERMA;

HEXAPODA; TROGODERMA;

EID: 63549085149     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.02.064     Document Type: Article

References (29)

1. Mori K. Tetrahedron 65 (2009) 2798-2805
2. Silverstein R.M., Cassidy R.F., Burkholder W.E., Shapas T.J., Levinson H.Z., Levinson A.R., and Mori K. J. Chem. Ecol. 6 (1980) 911-917
3. Rodin J.O., Silverstein R.M., Burkholder W.E., and Gorman J.E. Science 165 (1969) 904-906
4. Mori K. Tetrahedron Lett. (1973) 3869-3872
5. Mori K. Tetrahedron 30 (1974) 3817-3820
6. Mori K., Suguro T., and Uchida M. Tetrahedron 34 (1978) 3119-3123
7. Suguro T., and Mori K. Agric. Biol. Chem. 43 (1979) 409-410
8. Mori K., Kuwahara S., Levinson H.Z., and Levinson A.R. Tetrahedron 38 (1982) 2291-2297
9. Rossi R., and Carpita A. Tetrahedron 33 (1977) 2447-2450
10. Rossi R., Salvadori P.A., Carpita A., and Niccoli A. Tetrahedron 35 (1979) 2039-2042
11. Mori K. In: ApSimon J. (Ed). The Total Synthesis of Natural Products Vol. 9 (1992), Wiley, New York, NY 152-157
12. ® 4.1 (2008). (Sigma-Aldrich com./cheminars).
13. Blackwell H.E., O'Leary D.J., Chatterjee A.K., Washenfelder R.A., Bussmann D.A., and Grubbs R.H. J. Am. Chem. Soc. 122 (2000) 58-71
14. Chatterjee A.K., Choi T.-L., Sanders D.P., and Grubbs R.H. J. Am. Chem. Soc. 125 (2003) 11360-11370
15. Pederson R.L., Fellows J.M., Ung T.A., Ishihara H., and Hajela S.A. Adv. Synth. Catal. 344 (2002) 728-735
16. Mori, K.; Tashiro, T. Tetrahedron Lett., in press. doi:10.1016/j.tetlet.2009.02.046.
17. Shriner R.L., Adams R., and Marvel C.S. In: Gilman H. (Ed). Organic Chemistry, an Advanced Treatise Vol. 1 (1943), Wiley, New York, NY 298
18. Brewster J.H. In: Weissberger A. (Ed). Technique of Chemistry Vol. 4 (1972), Wiley-Interscience, New York, NY 111-129 Part III, Chapter XVII
19. Eliel E.L., and Wilen S.H. Stereochemistry of Organic Compounds (1994), Wiley, New York, NY pp 1071-1093
20. Polavarapu P.L. Chem. Rec. 7 (2007) 125-136
21. Taniguchi, T.; Monde, K.; Schlingmann, G.; Nakanishi, K.; Berova, N. Symposium Papers, 50th Symposium on the Chemistry of Natural Products, Fukuoka, Sep 30-Oct 2, 2008; pp 281-284.
22. Taniguchi T., Monde K., Nakanishi K., and Berova N. Org. Biomol. Chem. 6 (2008) 4399-4405
23. Hashimoto H., and Tatehara T. Jpn. Tokkyo Kokai (2005) 348727
24. Fouquet C., and Schlosser M. Angew. Chem., Int. Ed. Engl. 13 (1974) 82-83
25. McLafferty F.W. Wiley Registry of Mass Spectral Data, 7th Ed. with NIST 2005 Spectral Data (Upgrade) (2005), Wiley, New York, NY (CD-ROM)
26. Marukawa K., Takikawa H., and Mori K. Biosci. Biotechnol. Biochem. 65 (2001) 305-314
27. Seki M., and Mori K. Eur. J. Org. Chem. (2001) 503-506
28. Tamogami S., Awano K., Amaike M., Takagi Y., and Kitahara T. Flavour Fragrance J. 16 (2001) 349-352
29. Grubbs II (not Grubbs I) catalyst was found by GC-MS to cause extensive olefin isomerizations at 60 °C and less in the case of acyclic diene metathesis (ADMET) polymerization, too: Fokou, P.-A.; Meier, M.-A.-R. J. Am. Chem. Soc. 2009, 131, 1664-1665.