Total syntheses of enantiomerically enriched R-(+)- And S-(-)-deplancheinef

Organic and Biomolecular Chemistry

Volumn 3, Issue 11, 2005, Pages 2140-2144

  Sydorenko, Nadiya ^a   Zificsak, Craig A ^a   Gerasyuto, Aleksey I ^a   Hsung, Richard P ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE ALKALOIDS; NATURAL PRODUCTS; SYNTHESIS FEATURES; TOTAL SYNTHESIS;

AMINO ACIDS; CONDENSATION; MOLECULAR STRUCTURE; OXIDATION; REACTION KINETICS; SYNTHESIS (CHEMICAL); YIELD STRESS;

AROMATIC COMPOUNDS;

DEPLANCHEINE; INDOLE ALKALOID;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

INDOLE ALKALOIDS; MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 20844437545     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b503862f     Document Type: Article

References (99)

1. Dictionary of Alkaloids, ed. I. W. Southern and J. Buckingham, Chapman and Hall, London, 1989.
2. (a) R. B. Herbert, in The Monoterpenoid Indole Alkaloids, supplement to volume 25, part 4 of The Chemistry of Heterocyclic Compounds, 3. E. Saxon, Wiley-Interscience, New York, 1994, ch. 1;
3. (b) J. E. Saxon, in The Monoterpenoid Indole Alkaloids, supplement to volume 25, part 4 of The Chemistry of Heterocyclic Compounds, ed. J. E. Saxon, Wiley-Interscience, New York, 1994, ch. 8.
4. (a) J. E. Saxon, in The Alkaloids, ed. G. A. Cordell, Academic Press, New York, 1998, vol. 50 and 51;
5. (b) M. Toyota and M. Ihara, Nat. Prod. Rep., 1998,15, 327;
6. (c) U. Scholz and E. Winterfeldt, Nat. Prod. Rep., 2000, 17, 349.
7. J. Bonjoch and D. Sole, Chem. Rev., 2000, 100, 3455.
8. A. I. Scott, Acc. Chem. Res., 1970, 3, 151.
9. (+)-Deplancheine (1) was initially isolated from the New Caledonian plant Alsloniadeplancheivan Heurck et Mueller Arg. (Apocynaceae). See: (a) R. Besselièvre, H. P. Cosson, B. C. Das and H. P. Husson, Tetrahedron Lett., 1980, 21, 63. For subsequent isolations, see:
10. (b) N. Petitfrere-Auvray, J. Vercauteren, G. Massiot, G. Lukacs, T. Sevenet, L. Le Men-Olivier, B. Richard and M. J. Jacquier, Phytochemistry, 1981, 20, 1987;
11. (c) D. Guillaume, A. M. Morfaux, B. Richard, G. Massiot, L. Le Men-Olivier, J. Pusset and T. Sevenet, Phytochemistry, 1984, 23, 2407;
12. (d) A. Cherif, G. Massiot, L. Le Men-Olivier, J. Pusset and S. Labarre, Phytochemistry, 1989, 28, 667;
13. (e) G.M.T. Robert, A. Ahond, C. Poupat, P. Potier, C. Jolies, A. Jousselin and H. Jacquemin, J. Nat. Prod., 1983, 46, 694.
14. J.-A. Duan, I. D. Williams, C.-T. Che, R.-H. Zhou and S.-X. Zhao, Tetrahedron Lett., 1999, 40, 2593.
15. (a) H. Rapoport, R. J. Windgassen, N. A. Hughes and T. P. Onak, J. Am. Chem. Soc., 1960, 82, 4404;
16. (b) E. Wenkert and B. Wickberg, J. Am. Chem. Soc., 1965, 87, 1580.
17. (a) P. A. Shore and A. Giachetti, Reserpine: Basic and Clinical Pharmacology in Handbook of Psychopharmacology, ed. L. L. Iversen, S. D. Eversen, S. H. Snyder, Plenum, New York, 1978, vol. 10, p. 197;
18. (b) J. M. Muller, E. Schlittler and H. J. Bein, Experientia, 1952, 8, 338;
19. (c) H. Pardell, Am. J. Cardiol., 1990, 65, 2H-5H;
20. (d) R. Betarbet, T. B. Sherer and J. T. Greenamyre, BioEssays, 2002, 24, 308.
21. C. Szántay, G. Blaskò, K. Honty and G. Dörnyei, Corynantheine, Yohimbine, and Related Alkaloids in The Alkaloids: Chemistry and Pharmacology, ed. A. Brossi, Academic, Orlando, 1986, vol. 27, p. 131.
22. J. Leonard, Nat. Prod. Rep., 1999, 16, 319.
23. For isolation, see: (a) S. R. Johns, J. A. Lamberton and J. L. Occolowitz, J. Chem. Soc., Chem. Commun., 1966, 421;
24. (b) S. R. Johns, J. A. Lamberton and J. L. Occolowitz, Aust. J. Chem., 1966, 19, 1951. For our recent total synthesis, see:
25. (c) Y. Zhang, R. P. Hsung, X. Zhang, J. Huang, B. W. Slafer and A. Davis, Org. Lett., 2005, 7, 1047.
26. For the most recent total syntheses, see: (a) S. M. Allin, C. I. Thomas, K. Doyle and M. R. J. Elsegood, J. Org. Chem., 2005, 70, 357;
27. (b) T. Itoh, Y. Matsuya, Y. Enomoto and A. Ohsawa, Heterocycles, 2001, 55, 1165;
28. (c) R. Lavilla, O. Coll, M. Nicolas, B. A. Sufi, J. Torrents and J. Bosch, Eur. J. Org. Chem., 1999, 2997;
29. (d) M. Lounasmaa, K. Karinen and A. Tolvanen, Heterocycles, 1997, 45, 1397;
30. (e) M. Lounasmaa, P. Hanhinen and R. Jokela, Heterocycles, 1996, 43, 443;
31. (f) B. Tirkkonen, J. Miettinen, J. Salo, R. Jokela and M. Lounasmaa, Tetrahedron, 1994, 50, 3537;
32. (g) P. Rosenmund and M. HosseiniMerescht, Liebigs Ann. Chem., 1992, 1321;
33. (K) P. J. Sankar, S. K. Das and V. S. Giri, Heterocycles, 1991, 32, 1109;
34. T. Fujii, M. Ohba and N. Sasaki, Chem. Pharm. Bull, 1989, 37, 2822;
35. (j) S. B. Mandal, V. S. Giri, M. S. Sabeena and S. C. Pakrashi, J. Org. Chem., 1988, 53, 4236;
36. (k) K. Takasu, N. Nishida, A. Tomimura and M. Ihara, J. Org. Chem., 2005, 70, ASAP.
37. For some earlier syntheses, see: (a) L. Calabi, B. Danieli, G. Lesma and G. Palmisano, Tetrahedron Lett., 1982, 23, 2139;
38. (b) L. E. Overman and T. C. Malone, J. Org. Chem., 1982, 47, 5297;
39. (c) M. Hämeilä and M. Lounasmaa, Acta Chem. Scand. Ser. B, 1981, 35, 217;
40. (d) W. R. Ashcroft and J. A. Joule, Tetrahedron Lett., 1980, 21, 2341;
41. (e) D. Thielke, J. Wegener and E. Winterfeldt, Angew. Chem., Int. Ed. Engl, 1974, 13, 602;
42. (f) M. L. Rueppel and H. Rapoport, J. Am. Chem. Suc., 1972, 94, 3877;
43. (g) K. E. Pfitzner and J. G. Moffatt, J. Am. Chem. Soc., 1963, 85, 3027.
44. For a total synthesis of S-(-)-deplancheine, see: A. I. Meyers, T. Sohda and M. F. Loewe, J. Org. Chem., 1986, 51, 3108. Also see ref. 13a.
45. For an excellent review, see: E. D. Cox and J. M. Cook, Chem. Rev., 1995, 95, 1797.
46. For some elegant examples of Pictet-Spengler cyclizations, see: (a) J. Yu, T. Wang, X. Liu, J. Deschamps, J. Flippen-Anderson, X. Liao and J. M. Cook, J. Org. Chem., 2003, 68, 7565;
47. (b) J. Yu, X. Wearing and J. M. Cook, Tetrahedron Lett., 2003,44, 543;
48. (c) J. Yu, T. Wang, X. Wearing, J. Ma and J. M. Cook, J. Org. Chem., 2003, 68, 5852;
49. (d) S. Zhao, X. Liao and J. M. Cook, Org. Lett., 2002, 4, 687.
50. For a recent example on catalytic asymmetric Pictet-Spengler cyclization, see: M. S. Taylor and E. N. Jacobsen, J. Am. Chem. Soc., 2004, 126, 10558.
51. For reviews, see: (a) R. P. Hsung, A. V. Kurdyumov and N. Sydorenko, Eur. J. Org. Chem., 2005, 23;
52. (b) H. A. Coverdale and R. P. Hsung, Chemtracts, 2003, 16, 238;
53. (c) R. P. Hsung, L.-L. Wei, H. M. Sklenicka, H. C. Shen, M. J. McLaughlin and L. R. Zehnder, Trends in Heterocyclic Chemistry, Research Trends, Poojapura, Trivandrum, India, 2001, vol. 7, p. 1.
54. For recent studies in this area, see: (a) K. M. Goodenough, W. J. Moran, P. Raubo and J. P. A. Harrity, J. Org. Chem., 2005, 70, 207;
55. (b) M. M. Abelman, J. K. Curtis and D. R. James, Tetrahedron Lett., 2003, 44, 6527;
56. (c) S. J. Hedley, W. J. Moran, D. A. Price and J. P. A. Harrity, J. Org. Chem., 2003, 68, 4286;
57. (d) M.-Y. Chang, J. Y.-C. Lin, S. T. Chen and N.-C. Chang, J. Chin. Chem. Soc., 2002, 49, 1079;
58. (e) S. J. Hedley, W. J. Moran, A. H. G. P. Prenzel, D. A. Price and J. P. A. Harrity, Synlett, 2001, 1596;
59. (f) I. W. Davies, J.-F. Marcoux and P. J. Reider, Org. Lett., 2001, 3, 209;
60. (g) I. W. Davies, M. Taylor, J.-F. Marcoux, J. Wu, P. G. Dormer, D. Hughes and P. J. Reider, J. Org. Chem., 2001, 66, 251;
61. (h) P. Nemes, B. Balázs, G. Tóth and P. Scheiber, Synlett, 1999, 222;
62. (i) D. H. Hua, Y. Chen, H.-S. Sin, P. D. Robinson, C. Y. Meyers, E. M. Perchellet, J.-P. Perchellet, P. K. Chiang and J.-P. Biellmann, Acta Crystallogr., Sect. C, 1999, 55, 1698;
63. (j) P. Benovsky, G. A. Stephenson and J. R. Stille, J. Am. Chem. Soc., 1998, 120, 2493;
64. (k) D. Heber and Th. Berghaus, J. Heterocyd. Chem., 1994, 31, 1353;
65. (l) K. Paulvannan and J. R. Stille, Tetrahedron Lett., 1993, 34, 215;
66. K. Paulvannan and J. R. Stille, Tetrahedron Lett., 1993, 34, 6677.
67. N. Sydorenko, R. P. Hsung, O. S. Darwish, J. M. Hahn and J. Liu, J. Org. Chem., 2004, 69, 6732.
68. (a) H. M. Sklenicka, R. P. Hsung, M. J. McLaughlin, L.-L. Wei, A. I. Gerasyuto and W. W. Brennessel, J. Am. Chem. Soc., 2002, 124, 10435;
69. (b) H. M. Sklenicka, R. P. Hsung, L.-L. Wei, M. J. McLaughlin, A. I. Gerasyuto, S. J. Degen and J. A. Mulder, Org. Lett., 2000, 2, 1161;
70. (c) R. P. Hsung, L.-L. Wei, H. M. Sklenicka, C. J. Douglas, M. J. McLaughlin, J. A. Mulder and L. J. Yao, Org. Lett., 1999, 1, 509.
71. For intramolecular formal aza-[3 + 3] cycloaddition, see: L.-L. Wei, H. M. Sklenicka, A. I. Gerasyuto and R. P. Hsung, Angew. Chem., Int. Ed., 2001, 40, 1516.
72. M. J. McLaughlin, R. P. Hsung, K. C. Cole, J. M. Hahn and J. Wang, Org. Lett., 2002, 4, 2017.
73. S. Luo, C. A. Zificsak and R. P. Hsung, Org. Lett., 2003, 5, 4709.
74. For two other total syntheses of tangutorine, see: (a) S. Luo, J. Zhao and H. Zhai, J. Org. Chem., 2004, 69, 4548;
75. (b) T. Putkonen, A. Tolvanen, R. Jokela, S. Caccamese and N. Parrinelloc, Tetrahedron, 2003, 59, 8589 and references cited therein.
76. S. Kobayashi, T. Ueda and T. Fukuyama, Synlett, 2000, 883.
77. (a) R. L. Parsons, J. D. Berk and M. E. Kuehne, J. Org. Chem., 1993, 58, 7482;
78. (b) K. M. Czerwinski and C. A. Zificsak, unpublished results.
79. For a review of palladium coupling reactions of heterocycles, including indoles, see: J. J. Li and G. W. Gribble, Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist, Tetrahedron Organic-Chemistry Series Vol. 20, Elsevier, Oxford UK, 2000.
80. K. Sonogashira, in Metal-Catalyzed Cross-Coupling Reactions, ed. F. Diederich and P. J. Stang, Wiley-VCH, Weinheim, Germany, 1998, p. 203.
81. P. A. Wender, S. M. Sieburth, J. J. Petraitis and S. K. Singh, Tetrahedron, 1981, 37, 3967.
82. G. Oddon and D. Uguen, Tetrahedron Lett., 1998, 39, 1153.
83. V. Farina, V. Krishnamurthy and W. J. Scott, Org. React., 1997, 50, 1.
84. H. Kapnang and G. Charles, Tetrahedron Lett., 1983, 24, 3233.
85. L. Chu, M. H. Fisher, M. T. Goulet and M. J. Wyvratt, Tetrahedron Lett., 1997, 38, 3871.
86. N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457.
87. W. R. Roush, personal communication.
88. The boronic acid has been described but without experimental detail, see: (a) J. Uenishi, R. Kawahama, O. Yonemitsu, A. Wada and M. Ito, Angew. Chem., Int. Ed., 1998, 37, 320;
89. (b) W. R. Roush, J. A. Champoux and B. C. Peterson, Tetrahedron Lett., 1996, 37, 8989.
90. R. F. Heck, Org. React., 1982, 27, 345.
91. A. F. Littke and G. C. Fu, J. Am. Chem. Soc., 2001, 123, 6989.
92. J. O. Osby, M. G. Martin and B. Ganem, Tetrahedron Lett., 1984, 25, 2093.
93. J. D. Winkler, J. Axten, A. H. Hammach, Y.-S. Kwak, U. Lengweiler, M. J. Lucero and K. N. Houk, Tetrahedron, 1998, 54, 7045.
94. D. M. Burness, J. Org. Chem., 1956, 21, 97.
95. H.-J. Teuberand R. Quintanilla-Licea, J. Prakt. Chem./Chem.-Ztg., 1994, 336, 452.
96. (a) R. N. Schul, Chem. Ind. (London), 1960, 1246-1247;
97. (b) For the preparation of the sodium salt, see: W. S. Johnson, E. Woroch and F. J. Mathews, J. Am. Chem. Soc., 1947, 69, 566.
98. A. I. Gerasyuto, R. P. Hsung, N. Sydorenko and B. W. Slafer, J. Org. Chem., 2005, 70, ASAP.
99. Enantiomeric ratios were determined on an Agilent HPLC instrument equipped with a Chiralcel OD column.