Synthesis of the reported structure of trans-africanan-1α-ol

Journal of Organic Chemistry

Volumn 76, Issue 23, 2011, Pages 9733-9737

  Taber, Douglass F ^a   Bai, Sha ^a   Tian, Weiwei ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETO ESTER; NATURAL PRODUCTS; SESQUITERPENES; SYNTHETIC MATERIALS;

CHEMISTRY;

ORGANIC COMPOUNDS;

AFRICANAN 1ALPHA OL; CYCLOPENTANE DERIVATIVE; SESQUITERPENE; UNCLASSIFIED DRUG;

ARGENTINA; ARTICLE; ASTHMA; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; LIPPIA; LIPPIA INTEGRIFOLIA; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TRADITIONAL MEDICINE;

LIPPIA; MOLECULAR STRUCTURE; SESQUITERPENES;

EID: 82255179728     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo2018558     Document Type: Article

References (32)

1. Coronel, A. C.; Cerda-García-Rojas, C. M.; Joseph-Nathan, P.; Catalan, C. A. N. Flavour Fragrance J. 2006, 21, 839-847
2. Nakamura, K.; Kawai, Y.; Ohno, A. Tetrahedron Lett. 1990, 31, 267-270
3. Fujisawa, T.; Mobele, B. I.; Shimizu, M. Tetrahedron Lett. 1991, 32, 7055-7058
4. Medson, C.; Smallridge, A. J.; Trewhella, M. A. Tetrahedron: Asymmetry 1997, 8, 1049-1054
5. For a related Ru BINAP reduction of a cyclic β-keto ester, see: Taber, D. F.; Wang, Y. J. Am. Chem. Soc. 1997, 119, 22-26
6. Yates, P.; Jorgenson, M. J.; Singh, P. J. Am. Chem. Soc. 1969, 91, 4739-4748
7. Marx, J. N.; Norman, L. R.; Cox, J. H. J. Org. Chem. 1972, 37, 4489-4491
8. Marx, J. N.; Norman, L. R. J. Org. Chem. 1975, 40, 1602-1606
9. Urban, E.; Knühl, G.; Helmchen, G. Tetrahedron 1996, 52, 971-986
10. Schiaffo, C. E.; Dussault, P. H. J. Org. Chem. 2008, 73, 4688-4690
11. For the development of aliphatic nitrile alkylations, see: Taber, D. F.; Kong, S. J. Org. Chem. 1997, 62, 8575-8576
12. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392-4398
13. Yang, Y.; Li, W. Z. J. Org. Chem. 2005, 70, 8224-8227
14. Wang, X.; Bowman, E. J.; Bowman, B. J.; Porco, J. A., Jr. Angew. Chem., Int. Ed. 2004, 43, 3601-3605
15. Hansen, E. C.; Lee, D. Org. Lett. 2004, 6, 2035-2038
16. Hoye, T. R.; Jeffrey, C. S.; Tennakoon, M. A.; Wang, J.; Zhao, H. J. Am. Chem. Soc. 2004, 126, 10210-10211
17. Grieco, P. A.; Oguri, T.; Wang, C. J.; Williams, E. J. Org. Chem. 1977, 42, 4113-4118
18. Molander, G. A.; Harring, L. S. J. Org. Chem. 1989, 54, 3525-3532
19. For a previous example of syn cyclopropanation of a cycloheptenol, see: Mash, E. A.; Gregg, T. M.; Kaczynski, M. A. J. Org. Chem. 1996, 61, 2743-2752
20. Furukawa, J.; Kawabata, R.; Nishimura, J. Tetrahedron Lett. 1966, 7, 3353-3354
21. Charette, A. B.; Lebel, H. J. Org. Chem. 1995, 60, 2966-2967
22. Schmuff, N. R.; Trost, B. M. J. Org. Chem. 1983, 48, 1404-1412
23. Shirahama, H.; Hayano, K.; Kanemoto, Y.; Misumi, S.; Ohtsuka, T.; Hashiba, N.; Furusaki, A.; Murata, S.; Noyori, R.; Matsumoto, T. Tetrahedron Lett. 1980, 21, 4835-4838
24. Paquette, L. A.; Ham, W. H. Tetrahedron Lett. 1986, 27, 2341-2344
25. Paquette, L. A.; Ham, W. H. J. Am. Chem. Soc. 1987, 109, 3025-3036
26. Fan, W.; White, J. B. J. Org. Chem. 1993, 58, 3557-3562
27. Cossy, J.; BouzBouz, S.; Mouza, C. Synlett 1998, 621-622
28. Marques, F.; Ferreira, J. T. B.; Piers, E. J. Braz. Chem. Soc. 2000, 11, 502-511
29. Matsuda, Y.; Endo, Y.; Saikawa, Y.; Nakata, M. J. Org. Chem. 2011, 76, 6258-6263
30. Sugimura, T.; Futagawa, T.; Tai, A. Chem. Lett. 1990, 19, 2295-2298
31. Paquette, L. A.; Arbit, R. M.; Funel, J.-A.; Bolshakov, S. Synthesis 2002, 2105-2109
32. Weatherhead, G. S.; Cortez, G. A.; Schrock, R. R.; Hoveyda, A. H. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 5805-5809