Chiral benzyl centers through asymmetric catalysis. A three-step synthesis of (R)-(-)-α-curcumene via asymmetric hydrovinylation

Organic Letters

Volumn 6, Issue 18, 2004, Pages 3159-3161

  Zhang, Aibin ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CURCUMENE; BENZYL DERIVATIVE; ESSENTIAL OIL; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; ASYMMETRIC HYDROVINYLATION; CATALYSIS; CHEMICAL MODIFICATION; DRUG SYNTHESIS; SUZUKI REACTION;

BENZENE DERIVATIVES; CATALYSIS; CURCUMIN; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 4544228993     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048790v     Document Type: Article

References (42)

1. For recent references, see the following and others cited therein. (a) Bisabolanes: Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 895. Vyvyan, J. R.; Loitz, C.; Looper, R. E.; Mattingly, C. S.; Peterson, E. A.; Staben, S. T. J. Org. Chem. 2004, 69, 2461. (b) Heliannanes: Kishuku, H.; Shindo, M.; Shishido, K. Chem. Commun. 2003, 350. (c) Pseudopterosins: Look, S. A.; Fenical, W.; Jacobs, R. S.; Clardy, J. Proc. Natl. Acad. Sci. 1986, 83, 6238. Johnson, T. W.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 13486. Harrowven, D. C.; Tyte, M. J. Tetrahedron Lett. 2004, 45, 2089. (d) Serrulatanes: Rodriguez, A.; Ramirez, C. J. Nat. Prod. 2001, 64, 100. Dehmel, F.; Lex, J.; Schmalz, H.-G. Org. Lett. 2002, 4, 3915.
2. For recent references, see the following and others cited therein. (a) Bisabolanes: Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 895. Vyvyan, J. R.; Loitz, C.; Looper, R. E.; Mattingly, C. S.; Peterson, E. A.; Staben, S. T. J. Org. Chem. 2004, 69, 2461. (b) Heliannanes: Kishuku, H.; Shindo, M.; Shishido, K. Chem. Commun. 2003, 350. (c) Pseudopterosins: Look, S. A.; Fenical, W.; Jacobs, R. S.; Clardy, J. Proc. Natl. Acad. Sci. 1986, 83, 6238. Johnson, T. W.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 13486. Harrowven, D. C.; Tyte, M. J. Tetrahedron Lett. 2004, 45, 2089. (d) Serrulatanes: Rodriguez, A.; Ramirez, C. J. Nat. Prod. 2001, 64, 100. Dehmel, F.; Lex, J.; Schmalz, H.-G. Org. Lett. 2002, 4, 3915.
3. For recent references, see the following and others cited therein. (a) Bisabolanes: Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 895. Vyvyan, J. R.; Loitz, C.; Looper, R. E.; Mattingly, C. S.; Peterson, E. A.; Staben, S. T. J. Org. Chem. 2004, 69, 2461. (b) Heliannanes: Kishuku, H.; Shindo, M.; Shishido, K. Chem. Commun. 2003, 350. (c) Pseudopterosins: Look, S. A.; Fenical, W.; Jacobs, R. S.; Clardy, J. Proc. Natl. Acad. Sci. 1986, 83, 6238. Johnson, T. W.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 13486. Harrowven, D. C.; Tyte, M. J. Tetrahedron Lett. 2004, 45, 2089. (d) Serrulatanes: Rodriguez, A.; Ramirez, C. J. Nat. Prod. 2001, 64, 100. Dehmel, F.; Lex, J.; Schmalz, H.-G. Org. Lett. 2002, 4, 3915.
4. For recent references, see the following and others cited therein. (a) Bisabolanes: Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 895. Vyvyan, J. R.; Loitz, C.; Looper, R. E.; Mattingly, C. S.; Peterson, E. A.; Staben, S. T. J. Org. Chem. 2004, 69, 2461. (b) Heliannanes: Kishuku, H.; Shindo, M.; Shishido, K. Chem. Commun. 2003, 350. (c) Pseudopterosins: Look, S. A.; Fenical, W.; Jacobs, R. S.; Clardy, J. Proc. Natl. Acad. Sci. 1986, 83, 6238. Johnson, T. W.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 13486. Harrowven, D. C.; Tyte, M. J. Tetrahedron Lett. 2004, 45, 2089. (d) Serrulatanes: Rodriguez, A.; Ramirez, C. J. Nat. Prod. 2001, 64, 100. Dehmel, F.; Lex, J.; Schmalz, H.-G. Org. Lett. 2002, 4, 3915.
5. For recent references, see the following and others cited therein. (a) Bisabolanes: Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 895. Vyvyan, J. R.; Loitz, C.; Looper, R. E.; Mattingly, C. S.; Peterson, E. A.; Staben, S. T. J. Org. Chem. 2004, 69, 2461. (b) Heliannanes: Kishuku, H.; Shindo, M.; Shishido, K. Chem. Commun. 2003, 350. (c) Pseudopterosins: Look, S. A.; Fenical, W.; Jacobs, R. S.; Clardy, J. Proc. Natl. Acad. Sci. 1986, 83, 6238. Johnson, T. W.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 13486. Harrowven, D. C.; Tyte, M. J. Tetrahedron Lett. 2004, 45, 2089. (d) Serrulatanes: Rodriguez, A.; Ramirez, C. J. Nat. Prod. 2001, 64, 100. Dehmel, F.; Lex, J.; Schmalz, H.-G. Org. Lett. 2002, 4, 3915.
6. For recent references, see the following and others cited therein. (a) Bisabolanes: Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 895. Vyvyan, J. R.; Loitz, C.; Looper, R. E.; Mattingly, C. S.; Peterson, E. A.; Staben, S. T. J. Org. Chem. 2004, 69, 2461. (b) Heliannanes: Kishuku, H.; Shindo, M.; Shishido, K. Chem. Commun. 2003, 350. (c) Pseudopterosins: Look, S. A.; Fenical, W.; Jacobs, R. S.; Clardy, J. Proc. Natl. Acad. Sci. 1986, 83, 6238. Johnson, T. W.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 13486. Harrowven, D. C.; Tyte, M. J. Tetrahedron Lett. 2004, 45, 2089. (d) Serrulatanes: Rodriguez, A.; Ramirez, C. J. Nat. Prod. 2001, 64, 100. Dehmel, F.; Lex, J.; Schmalz, H.-G. Org. Lett. 2002, 4, 3915.
7. For recent references, see the following and others cited therein. (a) Bisabolanes: Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 895. Vyvyan, J. R.; Loitz, C.; Looper, R. E.; Mattingly, C. S.; Peterson, E. A.; Staben, S. T. J. Org. Chem. 2004, 69, 2461. (b) Heliannanes: Kishuku, H.; Shindo, M.; Shishido, K. Chem. Commun. 2003, 350. (c) Pseudopterosins: Look, S. A.; Fenical, W.; Jacobs, R. S.; Clardy, J. Proc. Natl. Acad. Sci. 1986, 83, 6238. Johnson, T. W.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 13486. Harrowven, D. C.; Tyte, M. J. Tetrahedron Lett. 2004, 45, 2089. (d) Serrulatanes: Rodriguez, A.; Ramirez, C. J. Nat. Prod. 2001, 64, 100. Dehmel, F.; Lex, J.; Schmalz, H.-G. Org. Lett. 2002, 4, 3915.
8. For recent references, see the following and others cited therein. (a) Bisabolanes: Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 895. Vyvyan, J. R.; Loitz, C.; Looper, R. E.; Mattingly, C. S.; Peterson, E. A.; Staben, S. T. J. Org. Chem. 2004, 69, 2461. (b) Heliannanes: Kishuku, H.; Shindo, M.; Shishido, K. Chem. Commun. 2003, 350. (c) Pseudopterosins: Look, S. A.; Fenical, W.; Jacobs, R. S.; Clardy, J. Proc. Natl. Acad. Sci. 1986, 83, 6238. Johnson, T. W.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 13486. Harrowven, D. C.; Tyte, M. J. Tetrahedron Lett. 2004, 45, 2089. (d) Serrulatanes: Rodriguez, A.; Ramirez, C. J. Nat. Prod. 2001, 64, 100. Dehmel, F.; Lex, J.; Schmalz, H.-G. Org. Lett. 2002, 4, 3915.
9. (a) Bohlman, F.; Lonitz, M. Chem. Ber. 1978, 111, 843.
10. (b) McEnroe, F. J.; Fenical, W. Tetrahedron 1978, 34, 1661.
11. (c) Fusetani, N.; Sugano, M.; Matsunaga, S.; Hashimoto, K. Experientia 1987, 43, 1234.
12. (d) Wright, A. E.; Pomponi, S. A.; McConnell, O. J.; Kohmoto, S.; McCarthy, P. J. J. Nat. Prod. 1987, 50, 976.
13. (e) Ohno, M.; Todoriki, R.; Yamamoto, Y.; Akita, H. Chem. Pharm. Bull. 1994, 42, 1590.
14. (f) Asaoka, M.; Shima, K.; Fujii, N.; Takei, H. Tetrahedron 1988, 44, 4757.
15. (g) Rucker, G.; Breitmaier, E.; Manns, D.; Maier, W.; Marek, A.; Heinzmann, B.; Heiden, K.; Seggewies, S. Arch. Pharm. 1997, 330, 12.
16. (h) Mayer, A. M. S.; Jacobson, P. B.; Fenical, W.; Jacobs, R. S.; Glaser, K. B. Life Sci. 1998, 62, 401.
17. 2Zn was used in synthesis of the serrulatane diterpene erogorgiaene, see: Cesati, R. R.; de Armas, J.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 96.
18. Enzymatic or microbial methods: (a) Fuganti, C.; Serra, S. Synlett 1998, 1252. (b) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279.
19. Enzymatic or microbial methods: (a) Fuganti, C.; Serra, S. Synlett 1998, 1252. (b) Fuganti, C.; Serra, S.; Dulio, A. J. Chem. Soc., Perkin Trans. 1 1999, 279.
20. Meyers, A. I.; Stoianova, D. J. Org. Chem. 1997, 62, 5219.
21. Hagiwara, H.; Okabe, T.; Ono, H.; Kamat, V. P.; Hoshi, T.; Suzuki, T.; Ando, M. J. Chem. Soc., Perkin Trans. 1 2002, 895.
22. Harmata, M.; Hong, X.; Barnes, C. L. Tetrahedron Lett. 2003, 44, 7261.
23. Schmalz, H.-G.; de Koning, C. B.; Bernicke, D.; Siegel, S.; Pfletschinger, A. Angew. Chem., Int. Ed. 1999, 38, 1620.
24. Takano, S.; Yanase, M.; Sugihara, T.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1988, 1538.
25. Tamao, K.; Hayashi, T.; Matsumoto, H.; Yamamato, H.; Kumada, M. Tetrahedron Lett. 1979, 20, 2155.
26. 3) for material of 90% ee as determined by HPLC. For a compilation of various values, see ref 7. In this paper we report values based on HPLC of key intermediates, which are further corroborated by optical rotations.
27. (a) RajanBabu, T. V. Chem. Rev. 2003, 103, 2845.
28. (b) Nandi, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899.
29. (c) Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 2002, 124, 734.
30. (d) Zhang, A. RajanBabu, T. V. Org. Lett. 2004, 6, 1515.
31. (e) For review of classical work on hydrovinylation, see also: Jolly, P. W.; Wilke, G. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: New York, 1996; Vol. 2, p. 1024.
32. Li, A.; Yue, G.; Li, Y.; Pan, X.; Yang, T.-K. Tetrahedron: Asymmetry 2003, 14, 75.
33. (a) Nomura, N.; Jin, J.; Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 459.
34. (b) RajanBabu, T. V.; Nomura, N.; Jin, J.; Nandi, M.; Park, H.; Sun, X. J. Org. Chem. 2003, 68, 8431.
35. Nandi, M.; Jin, J.; RajanBabu, T. V. J. Am. Chem. Soc. 1999, 121, 9899.
36. Park, H.; RajanBabu, T. V. J. Am. Chem. Soc. 2002, 124, 734.
37. Franció, G.; Faraone, F.; Leitner, W. J. Am. Chem. Soc. 2002, 124, 736.
38. Zhang, A.; RajanBabu, T. V. Org. Lett. 2004, 6, 1515.
39. See Supporting information for procedures and chromatographic and spectroscopic data.
40. See ref 11.
41. N2-diaplacement on the tosylate of 7 with various copper reagents failed in our hands. The Cu-catalyzed reaction of the corresponding iodide with 2-methyl-1-propenylmagnesium bromide was also capricious.
42. +/ acetone, Dess-Martin reagent gave unacceptable yields.