Flexible access to monoterpenoid indole alkaloids using a cyclopentanoid chiral building block

Heterocycles

Volumn 77, Issue 2, 2009, Pages 855-863

  Hayashi, Masato ^a   Motosawa, Keiichi ^a   Satoh, Atsushi ^a   Shibuya, Masatoshi ^a   Ogasawara, Kunio ^a   Iwabuchi, Yoshiharu ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Chiral Building Block; Diastereocontrolled Synthesis; Enantiocontrolled Synthesis; Monoterpenoid Indole Alkaloid; Total Synthesis

Indexed keywords

EID: 77955675175     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(F)120     Document Type: Article

References (59)

1. H. Nakashima, M. Sato, T. Taniguchi, and K. Ogasawara Synthesis 2000 817
2. H. Nakashima, M. Sato, T. Taniguchi, and K. Ogasawara Tetrahedron Lett. 41 2000 2639
3. K. Tanaka, H. Nakashima, T. Taniguchi, and K. Ogasawara Org. Lett. 2 2000 1915
4. K. Tanaka, T. Taniguchi, and K. Ogasawara Tetrahedron Lett. 42 2001 1049
5. M. Hayashi, T. Unno, M. Takahashi, and K. Ogasawara Tetrahedron Lett. 43 2002 1461
6. J. Stckigt, and M. Ruppert D. Barton, K. Nakanishi, Comprehensive Natural Products Vol. 4 1999 Elsevier New York 109
7. J.E. Saxton G.A. Cordell, The Alkaloids Vol. 51 1998 Academic Press New York Chapter 1
8. Enantiocontrolled synthesis of (+)-20R-15, 20-dihydrocleavamine, see B. Danieli, G. Lesma, D. Passarella, and A. Silvani Tetrahedron Lett. 41 2000 3489
9. R.M. Kanada, and K. Ogasawara Tetrahedron Lett. 42 2001 7311
10. M. Amat, C. Escolano, O. Lozano, N. Llor, and J. Bosch Org. Lett. 5 2003 3139
11. For selected total synthesis of (-)-eburnamonine, see S. Takano, M. Yonaga, M. Morimoto, and K. Ogasawara J. Chem. Soc., Perkin Trans. 1 1985 305
12. A.G. Schultz, and L. Pettus J. Org. Chem. 62 1997 6855
13. A.G.H. Wee, and Q. Yu Tetrahedron Lett. 41 2000 587
14. W.G.H. Andrew, and Y. Qing J. Org. Chem. 66 2001 8935
15. Y. Murakami, M. Shindo, and K. Shishido Synlett 2005 664
16. For selected enantiocontrolled synthesis of aspidospermidine, see M. Node, H. Nagasawa, and K. Fuji J. Org. Chem. 55 1990 517
17. D. Desmale, and J. d'Angelo J. Org. Chem. 59 1994 2292
18. A.G. Schultz, and L. Pettus J. Org. Chem. 62 1997 6855
19. S.A. Kozmin, T. Iwama, Y. Huang, and V.H. Rawal J. Am. Chem. Soc. 124 2002 4628
20. J.P. Marino, M.B. Rubio, G. Cao, and A. de Bois J. Am. Chem. Soc. 124 2002 13398
21. R. Iyengar, K. Schildknegt, and J. Aub Org. Lett. 2 2000 1625
22. For recent total synthesis of Aspidosperma alkaloids, see F. He, Y. Bo, J.D. Altom, and E.J. Corey J. Am. Chem. Soc. 121 1999 6771
23. M.A. Toczko, and C.H. Heathcock J. Org. Chem. 65 2000 2642
24. Y. Fukuda, M. Shindo, and K. Shishido Org. Lett. 5 2003 749
25. L.A. Sharp, and S.Z. Zard Org. Lett. 8 2006 831
26. I. Coldham, A.J.M. Burrell, L.E. White, H. Adams, and N. Oram Angew. Chem. Int. Ed. 46 2007 6159
27. J. Harley-Mason, and M. Kaplan Chem. Commun. 1967 915
28. M. Frigerio, and M. Santagosino Tetrahedon Lett. 35 1994 8019
29. M. Frigerio, M. Santagosino, S. Sputore, and G. Palmisano J. Org. Chem. 60 1995 7272
30. Previously, the conversion of 1 to 8 was conducted by a two step sequence consisting of (i) Dess-Martin periodinane-mediated oxidation to give 7, and (ii) warming 7 in acetic acid to promote the β-elimination of a cumyl alcohol; see ref. 1. The facile one-pot conversion of 1 to 8 features the inherent acidic nature of IBX in DMSO. For the discussion on pKa of IBX, see M.J. Gallen, R. Goumont, T. Clark, F. Terrier, and C.M. Williams Angew. Chem. Int. Ed. 45 2006 2929
31. J.-L. Luche J. Am. Chem. Soc. 100 1978 2226
32. A.L. Gemal, and J.-L. Luche J. Am. Chem. Soc. 103 1981 5454
33. A.E. Wick, D. Felix, K. Steen, and A. Eschenmoser Helv. Chim. Acta 47 1964 2425
34. H. Nakashima, M. Sato, T. Taniguchi, and K. Ogasawara Synlett 1999 1754
35. M. Hayashi, T. Unno, M. Takahashi, and K. Ogasawara Tetrahedron Lett. 43 2002 1461
36. S. Kim, and J.M. Lee Synth. Commun. 21 1991 25
37. For selected synthesis of (-)-dihydrocorynantheol; T. Suzuki, E. Sato, K. Unno, and T. Kametani Heterocycles 23 1985 835
38. R.L. Beard, and A.I. Meyers J. Org. Chem. 56 1991 2091
39. M. Ohba, T. Ohashi, and T. Fuji Heterocycles 32 1991 319
40. T. Itoh, M. Yokota, K. Miyauchi, K. Nagata, and A. Ohsawa Org. Lett. 8 2006 1533
41. A. Deiters, M. Pettersson, and S.F. Martin J. Org. Chem. 71 2006 6547
42. A. Tosaka, S. Itoh, N. Miyaszawa, M. Shibuya, K. Ogasawara, and Y. Iwabuchi Heterocycles 70 2006 153
43. For selected synthesis of antirhine, (±)-Antirhine: S. Takano, M. Takahashi, and K. Ogasawara J. Am. Chem. Soc. 102 1980 4282
44. (-)-Antirhine: S. Takano, N. Tamura, and K. Ogasawara J. Chem. Soc. Chem. Commun. 22 1981 1155
45. T. Suzuki, E. Sato, K. Unno, and T. Kametani Heterocycles 23 1985 839
46. T. Suzuki, E. Sato, K. Unno, and T. Kametani Chem. Pharm. Bull. 34 1986 3135
47. A. Pancrazi, J. Kervagoret, and Q. Khuong-Huu Tetrahedron Lett. 32 1991 4483
48. B. Danieli, G. Lesma, M. Mauro, G. Palmisano, and D. Passarella Tetrahedron Lett. 50 1994 8837
49. M. Kawamura, and K. Ogasawara Tetrahedron Lett. 36 1995 3369
50. G. Stork, and N.H. Baine J. Am. Chem. Soc. 104 1982 2321
51. G. Stork, and R. Mook Jr. J. Am. Chem. Soc. 105 1983 3720
52. A. Basha, M. Lipton, and S.M. Weinreb Tetrahedron Lett. 1977 4171
53. Y. Ito, T. Hirao, and T. Saegusa J. Org. Chem. 43 1978 1011
54. H.C. Brown, S.C. Kim, and S. Krishnamuthy J. Org. Chem. 45 1980 1
55. H. Tanaka, and K. Ogasawara Tetrahedron Lett. 43 2002 4417
56. S.V. Ley, J. Norman, W.P. Griffith, and S.P. Marsden Synthesis 1994 639
57. S. Torii, H. Tanaka, M. Taniguchi, and Y. Kameyama J. Org. Chem. 56 1991 3633
58. The prolongation of reaction time resulted in the attenuation of the diasteroselectivity in the Pictet-Spengler reaction of 34, suggesting that C(3) β-36 is the kinetically favored product.
59. G.F. Smith, and M.A. Wahid J. Chem. Soc. 1963 4002