Enantioselective access to (-)-indolizidines 167B, 209D, 239AB, 195B and (-)-monomorine from a common chiral synthon

Tetrahedron

Volumn 68, Issue 1, 2012, Pages 145-151

  Reddy, Chada Raji ^a   Latha, Bellamkonda ^a   Rao, Nagavaram Narsimha ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Chiral synthon; Horner Wadsworth Emmonsreaction; Indolizidine alkaloid; Reductive cyclization

Indexed keywords

1,3 DISUBSTITUTED FURO 3,4 B INDOLE; FURAN; INDOLE; RESIN; UNCLASSIFIED DRUG;

ALKYLATION; AROMATIZATION; ARTICLE; DEPROTECTION REACTION; DERIVATIZATION; ENANTIOSELECTIVITY; ION EXCHANGE; PRIORITY JOURNAL; PROTECTION;

EID: 82255183059     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.10.076     Document Type: Article

References (63)

1. J.W. Daly, T.F. Spande, and H.M. Garraffo J. Nat. Prod. 68 2005 1556 1575
2. T.H. Jones, H.L. Voegtle, H.M. Miras, R.G. Weatherford, T.F. Spande, H.M. Garraffo, J.W. Daly, D.W. Davidson, and R.R. Snelling J. Nat. Prod. 70 2007 160 168
3. J.P. Michael Nat. Prod. Rep. 24 2007 191 222
4. J.P. Michael Nat. Prod. Rep. 25 2008 139 165
5. P.-Q. Huang J. Royer, Asymmetric Synthesis of Nitrogen Heterocycles 2009 Wiley Weinheim
6. J.W. Daly, G.B. Brown, M. Mensahdwumah, and C.W. Myers Toxicon 16 1978 163 188
7. V. Erspamer, and P. Melchiorri Trends Pharmacol. Sci. 1 1980 391 395
8. J.W. Daly, and T.F. Spande Alkaloids: Chem. Biol. Perspect. 4 1986 1 274
9. A.D. Elbein, and R.J. Molyneux Alkaloids 5 1987 Chapter 1
10. J.W. Daly, C.W. Myers, and N. Whittaker Toxicon 25 1987 1023 1095
11. A.B. Holmes, A.L. Smith, S.F. Williams, L.R. Hughes, Z. Lidert, and C. Swithenbank J. Org. Chem. 56 1991 1393 1405
12. N. Machinaga, and C. Kibayashi J. Org. Chem. 57 1992 5178 5189
13. J.J. Kiddle, D.L.C. Green, and C.M. Thompson Tetrahedron 51 1995 2851 2864
14. C. Celimene, H. Dhimane, A. Saboureau, and G. Lhommet Tetrahedron: Asymmetry 7 1996 1585 1588
15. R. Chenevert, G.M. Ziarani, and M. Dasser Heterocycles 51 1999 593 598
16. T.G. Back, and K. Nakajima Org. Lett. 1 1999 261 263
17. T.G. Back, and K. Nakajima J. Org. Chem. 65 2000 4543 4552
18. M. Amat, N. Llor, J. Hidalgo, C. Escolano, and J. Bosch J. Org. Chem. 68 2003 1919 1928
19. T.R. Varga, P. Nemes, Z. Mucsi, and P. Scheiber Tetrahedron Lett. 48 2007 1159 1161
20. G. Barbe, G. Pelletier, and A.B. Charette Org. Lett. 11 2009 3398 3401
21. C.R. Reddy, and N.N. Rao Tetrahedron Lett. 50 2009 2478 2480
22. S. Chandrasekhar, R.V.N.S. Murali, and C.R. Reddy Tetrahedron Lett. 50 2009 5686 5688
23. C.R. Reddy, N.N. Rao, and B. Srikanth Eur. J. Org. Chem. 2010 345 351
24. R.P. Polniaszek, and S.E. Belmont J. Org. Chem. 55 1990 4688 4693
25. E. Lee, K.S. Li, and J. Lim Tetrahedron Lett. 37 1996 1445 1446
26. S. Carbonnel, and Y. Troin Heterocycles 57 2002 1807 1830
27. J. Zaminer, C. Stapper, and S. Blechert Tetrahedron Lett. 43 2002 6739 6741
28. M.C. Corvo, and M.M.A. Pereira Tetrahedron Lett. 43 2002 455 458
29. P.G. Reddy, and S. Baskaran J. Org. Chem. 69 2004 3093 3101
30. L.F. Roa, D. Gnecco, A. Galindo, and J.L. Teran Tetrahedron: Asymmetry 15 2004 3393 3395
31. G. Guazzelli, R. Lazzaroni, and R. Settambolo Synthesis 2005 3119 3123
32. Z. Sun, S. Yu, Z. Ding, and D. Ma J. Am. Chem. Soc. 129 2007 9300 9301
33. D. Stead, P. Obrien, and A. Sanderson Org. Lett. 10 2008 1409 1412
34. A. Kapat, E. Nyfeler, G.T. Giuffredi, and P. Renaud J. Am. Chem. Soc. 131 2009 17746 17747
35. S. Gracia, R. Jerpan, S. Pellet-Rostaing, F. Popowycz, and M. Lemaire Tetrahedron Lett. 51 2010 6290 6293
36. Representative references for synthesis of (-)-209D
37. H. Takahata, M. Kubota, K. Ihara, N. Okamoto, T. Momose, N. Azer, A.T. Eldefrawi, and M.E. Eldefrawi Tetrahedron: Asymmetry 9 1998 3289 3301
38. N. Yamazaki, T. Ito, and C. Kibayashi Org. Lett. 2 2000 465 467
39. G. Kim, and E.J. Lee Tetrahedron: Asymmetry 12 2001 2073 2076
40. G. Kim, S. Jung, and W. Kim Org. Lett. 3 2001 2985 2987
41. N.T. Patil, N.K. Pahadi, and Y. Yamamoto Tetrahedron Lett. 46 2005 2101 2103
42. R.T. Yu, E.E. Lee, G. Malik, and T. Rovis Angew. Chem., Int. Ed. 48 2009 2379 2382
43. H. Liu, D. Su, G. Cheng, J. Xu, X. Wang, and Y. Hu Org. Biomol. Chem. 8 2010 1899 1904
44. For isolation of (-)-239AB see: M. Skrinjar, and L.G. Wistrand Tetrahedron Lett. 31 1990 1775 1778 For synthesis of (-)-239AB see
45. G.V. Thanh, J.-P. Celerier, and G. Lhommet Tetrahedron: Asymmetry 7 1996 2211 2212
46. C. Celimene, H. Dhimane, and G. Lhommet Tetrahedron 54 1998 10457 10468
47. H. Dhimane, C. Vanucci-Bacque, L. Hamon, and G. Lhommet Eur. J. Org. Chem. 9 1998 1955 1963
48. For isolation of (-)-195B see: M.W. Edwards, and J.W. Daly J. Nat. Prod. 51 1988 1188 1197 Representative references for synthesis of (-)-195B
49. S.R. Angle, and M. Kim J. Org. Chem. 72 2007 8791 8796
50. F.A. Davis, J. Zhang, and Y. Wu Tetrahedron Lett. 52 2011 2054 2057
51. Representative references for synthesis of (-)-monomorine
52. J. Royer, and H.P. Husson J. Org. Chem. 50 1985 670 673
53. C.W. Jefford, K. Sienkiewicz, and S.R. Thornton Tetrahedron Lett. 35 1994 4759 4762
54. S.H. Zhang, L. Xu, L. Miao, H. Shu, and M.L. Trudell J. Org. Chem. 72 2007 3133 3136
55. L.S. Pattenden, H. Adams, S.A. Smith, and J.P.A. Harrity Tetrahedron 64 2008 2951 2961
56. N. Toyooka, D.J. Zhou, and H. Nemoto J. Org. Chem. 73 2008 4575 4577
57. The similar aldehyde with different protecting groups is little explored. For references see: Ofuna, Y.; Hori, K. Jpn. Kokai Tokkyo Koho, JP 63063673 A 19880322, 1988.
58. H.P. Acharya, and D.L.J. Clive J. Org. Chem. 75 2010 5223 5233
59. Alvaro, G.; Amantini, D.; Castiglioni, E.; Fabio, R. D.; Pavone, F. PCT Int. Appl. WO 2010063662 A1 2010610, 2010.
60. J.M. Andres, E.M. Munoz, R. Pedrosa, and A. Perez-Encabo Eur. J. Org. Chem. 2003 3387 3397
61. Folker, L. Ger. Offen. DE2711010, 1978.
62. N.B. Kondekar, and P. Kumar Org. Lett. 11 2009 2611 2614
63. V. Jha, N.B. Kondekar, and P. Kumar Org. Lett. 12 2010 2762 2765