Catalytic enantioselective approach to the eudesmane sesquiterpenoids: Total synthesis of (+)-carissone

Organic Letters

Volumn 11, Issue 2, 2009, Pages 289-292

  Levine, Samantha R ^a   Krout, Michael R ^a   Stoltz, Brian M ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; CALCIUM CHANNEL BLOCKING AGENT; CARISSONE; PALLADIUM; SESQUITERPENE;

ARTICLE; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CALCIUM CHANNEL BLOCKERS; CATALYSIS; PALLADIUM; SESQUITERPENES, EUDESMANE; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 61449189803     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802409h     Document Type: Article

References (59)

1. For a comprehensive review of the eudesmane sesquiterpenoids of the Asteraceae family, see: Wu, Q.-X.; Shi, Y.-P.; Jia, Z.-J. Nat. Prod. Rep. 2006, 23, 699-734.
2. Fraga, B. M. Nat. Prod. Rep. 2007, 24, 1350-1381.
3. For the isolation and biological activity of (+)-carissone, see: (a) Mohr, K.; Schindler, O.; Reichstein, T. Helv. Chim. Acta 1954, 37, 462-471.
4. (b) Joshi, D. V.; Boyce, S. F. J. Org. Chem. 1957, 22, 95-97.
5. (c) Achenbach, H.; Waibel, R.; Addae-Mensah, I. Phytochemistry 1985, 24, 2325-2328.
6. (d) Lindsay, E. A.; Berry, Y.; Jamie, J. F.; Bremner, J. B. Phytochemistry 2000, 55, 403-406.
7. For the isolation and biological activity of (+)-3-oxocostusic acid, see: (a) Bohlmann, F.; Jakupovic, J.; Lonitz, M. Chem. Ber. 1977, 110, 301-314.
8. (b) Khanina, M. A.; Kulyyasov, A. T.; Bagryanskaya, I. Y.; Gatilov, Y. V.; Adekenov, S. M.; Raldugin, V. A. Chem. Nat. Compd. 1998, 34, 145-147.
9. (c) Al-Dabbas, M. M.; Hashinaga, F.; Abdelgaleil, S. A. M.; Suganuma, T.; Akiyama, K.; Hayashi, H. J. Ethnopharmacol. 2005, 97, 237-240.
10. (d) Mohamed, A. E.-H.; Ahmed, A. A.; Wollenweber, E.; Bohm, B.; Asakawa, Y. Chem. Pharm. Bull. 2006, 54, 152-155.
11. For the isolation and biological activity of a-eudesmol, see: (a) McQuillin, F. J.; Parrack, J. D. J. Chem. Soc. 1956, 2973-2978.
12. (b) Asakura, K.; Kanemasa, T.; Minagawa, K.; Kagawa, K.; Ninomiya, M. Brain Res. 1999, 823, 169-176.
13. (c) Toyota, M.; Yonehara, Y.; Horibe, I.; Minagawa, K.; Asakawa, Y. Phytochemistry 1999, 52, 689-694.
14. (d) Asakura, K.; Kanemasa, T.; Minagawa, K.; Kagawa, K.; Yagami, T.; Nakajima, M.; Ninomiya, M. Brain Res. 2000, 873, 94-101.
15. For syntheses of carissone, see: (a) Pinder, A. R.; Williams, R. A. J. Chem. Soc. 1963, 2773-2778.
16. (b) Sathe, V. M.; Rao, A. S. Indian J. Chem. 1971, 9, 95-97.
17. (c) Kutney, J. P.; Singh, A. K. Can. J. Chem. 1982, 60, 1842-1846.
18. (d) Wang, C.-C.; Kuoh, C.-S.; Wu, T.-S. J. Nat. Prod. 1996, 59, 409-411.
19. (e) Aoyama, Y.; Araki, Y.; Konoike, T. Synlett 2001, 9, 1452-1454.
20. For syntheses of 3-oxocostusic acid, see: (a) Ceccherelli, P.; Curini, M.; Marcotullio, M. C.; Rosati, O. Tetrahedron Lett. 1990, 31, 3071-3074.
21. (b) Xiong, Z.; Yang, J.; Li, Y. Tetrahedron: Asymmetry 1996, 7, 2607-2612.
22. For syntheses of α-eudesmol, see: (a) Humber, D. C.; Pinder, A. R.; Williams, R. A. J. Chem. Soc. 1967, 2335-2340.
23. (b) Taber, D. F.; Saleh, S. A. Tetrahedron Lett. 1982, 23, 2361-2364.
24. (c) Schwanz, M. A.; Willbrand, A. M. J. Org. Chem. 1985, 50, 1359-1365.
25. (d) Chou, T.-S.; Lee, S.-J.; Yao, N.-K. Tetrahedron 1989, 45, 4113-4124.
26. (e) Frey, B.; Hünig, S.; Koch, M.; Reissig, H.-U. Synlett 1991, 854-856.
27. (f) Frey, B.; Schnaubelt, J.; Reissig, H.-U. Eur. J. Org. Chem. 1999, 1385-1393.
28. For a review of enantioselective methodologies inspired by target-directed synthesis, see: Mohr, J. T.; Krout, M. R.: Stoltz, B. M. Nature 2008, 455, 323-332.
29. For reviews of the synthesis of quaternary stereocenters, see: (a) Cozzi, P. G.; Hilgraf, R.; Zimmermann, N. Eur. J. Org. Chem. 2007, 36, 5969-5994.
30. (b) Trost, B. M.; Jiang, C. Synthesis 2006, 369-396.
31. (c) Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis; Christoffers, J., Baro, A., Eds.; Wiley: Weinheim, 2005.
32. (d) Douglas, C. J.; Overman, L. E. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5363-5367.
33. (e) Denissova, I.; Barriault, L. Tetrahedron 2003, 59, 10105-10146.
34. (a) Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2004, 126, 15044-15055.
35. (b) Mohr, J. T.; Behenna, D. C.; Harned, A. M.; Stoltz, B. M. Angew. Chem., Int. Ed. 2005, 44, 6924-6927.
36. (c) Seto, M.; Roizen, J. L.; Stoltz, B. M. Angew. Chem., Int. Ed. 2008, 47, 6873-6876.
37. (d) For a review of the development of the enantioselective Tsuji allylation in our laboratory and others, see: Mohr, J. T.; Stoltz, B. M. Chem. - Asian J. 2007, 2, 1476-1491.
38. (a) McFadden, R. M.; Stoltz, B. M. J. Am. Chem. Soc. 2006, 128, 7738-7739.
39. (b) Behenna, D. C.; Stockdill, J. L.; Stoltz, B. M. Angew. Chem., Int. Ed. 2007, 46, 4077-4080.
40. (c) White, D. E.; Stewart, I. C.; Grubbs, R. H.; Stoltz, B. M. J. Am. Chem. Soc. 2008, 130, 810-811.
41. (d) Enquist, J. A., Jr.; Stoltz, B. M. Nature 2008, 453, 1228-1231.
42. Stork, G.; Danheiser, R. L. J. Org. Chem. 1973, 38, 1775-1776.
43. Trost, B. M.; Bream, R. N.; Xu, J. Angew. Chem., Int. Ed. 2006, 45, 3109-3112.
44. For the development of phosphinooxazoline (PHOX) ligands, see: (a) Helmchen, G.; Pfaltz, A. Acc. Chem. Res. 2000, 33, 336-345.
45. (b) Williams, J. M. J. Synlett 1996, 705-710.
46. Enol carbonate 9 was unstable to air, forming complex reaction mixtures that substantially affected yields and selectivities for the alkylation. Aromatic carbonate i was identified from this mixture. See the Supporting Information for more details. (Chemical Equation Presented) (17) The reactivity of β-ketoester (±)-10 contrasts significantly with that of related derivative (±)-ii, which generates iii in 79% yield and 86% ee under identical conditions. (Chemical Equation Presented)
47. β-Ketoester (±)-11 was recovered in 9% yield.
48. Breit, B.; Breuninger, D. J. Am. Chem. Soc. 2004, 126, 10244-10245.
49. Studies employing either allylmagnesium bromide generated from 16, MeLi, or MeMgBr nucleophiles were unsuccessful. Difficulties with these types of additions into vinylogous thioesters have been noted (see ref 14).
50. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
51. 2 in MeOH for this substrate.
52. The stereochemistry of (+)-20 was initially verified using NOE correlations. See the Supporting Information for details.
53. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155-4156.
54. (a) Lindgren, B. O.; Nilsson, T. Acta Chem. Scand. 1973, 27, 888-890.
55. (b) Kraus, G. A.; Roth, B. J. Org. Chem. 1980, 45, 4825-4830.
56. (c) Bal, B. S.; Childers, W. E.; Pinnick, H. W. Tetrahedron 1981, 37, 2091-2096.
57. Luche, J. L.; Gemal, A. L. J. Am. Chem. Soc. 1979, 101, 5848-5849.
58. Pinder, A. R.; Williams, R. A. J. Chem. Soc. 1963, 2773-2778.
59. For a related study, see: Petrova, K. V.; Mohr, J. T.; Stoltz, B. M. Org. Lett. 2009, 11, 293-296.