The efficient synthesis of morphinandienone alkaloids by using a combination of hypervalent iodine(III) reagent and heteropoly acid

Chemistry - A European Journal

Volumn 10, Issue 20, 2004, Pages 4977-4982

  Hamamoto, Hiromi ^a   Shiozaki, Yukiko ^a   Nambu, Hisanori ^a   Hata, Kayoko ^a   Tohma, Hirofumi ^a   Kita, Yasuyuki ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Alkaloids; C C coupling; Heteropoly acids; Hypervalent iodine reagents; Spiro compounds

Indexed keywords

AROMATIC COMPOUNDS; GELS; IODINE COMPOUNDS; ORGANIC ACIDS; OXIDATION; SILICA;

CHEMICAL OXIDIZING REAGENT SYSTEMS; COUPLING REACTIONS; SILICA GELS;

SYNTHESIS (CHEMICAL);

ACID; ALKALOID; GLAUCINE; IODINE; ISOQUINOLINE DERIVATIVE; LAUDANOSINE; MORPHINANDIENONE; OXIDIZING AGENT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CROSS COUPLING REACTION; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET RADIATION;

ACIDS; ALKALOIDS; IODINE; ISOQUINOLINES; MOLECULAR STRUCTURE; MORPHINANS; OXIDATION-REDUCTION;

EID: 7044222564     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200400358     Document Type: Article

References (67)

1. a) K. L. Stuart, Chem. Rev. 1971, 71, 47-72;
2. b) T. Kametani, K. Fukumoto, J. Heterocycl. Chem. 1971, 8, 341-356;
3. c) T. Kametani, K. Fukumoto, Synthesis 1972, 657-674;
4. d) T. Kametani, K. Fukumoto, F. Satoh, Bioorg. Chem. 1974, 3, 430-497;
5. e) G. Blaskó, G. A. Cordell, Heterocycles 1988, 27, 1269-1300.
6. O. P. Dhingra, in Oxidation in Organic Chemistry; (Ed.: W. S. Trahanovsky), Academic Press, New York, 1982, Part D, pp. 207-278.
7. a) B. Franck, G. Dunkelman, H. J. Lubs, Angew. Chem. 1967, 79, 1066-1067; Angew. Chem. Int. Ed. Engl. 1967, 6, 1075-1076;
8. a) B. Franck, G. Dunkelman, H. J. Lubs, Angew. Chem. 1967, 79, 1066-1067; Angew. Chem. Int. Ed. Engl. 1967, 6, 1075-1076;
9. b) T. Kametani, K. Fukumoto, A. Kozuka, H. Yagi, M. Koizumi, J. Chem. Soc. C 1969, 2034-2036;
10. c) G. Blaskó, G. Dörnyei, M. Bárczai-Bake, P. Péchy, C. Szántay, J. Org. Chem. 1984, 49, 1439-1441;
11. d) O. Hoshino, H. Ogasawara, M. Suzuki, M. Arasawa, B. Umezawa, Heterocycles 1990, 30, 385-388;
12. e) O. Hoshino, M. Suzuki, H. Ogasawara, Heterocycles 2000, 52, 751-760.
13. a) T. Kametani, K. Fukumoto, F. Satoh, H. Yagi, J. Chem. Soc. C 1969, 520-523;
14. b) T. Kametani, T. Sugahara, H. Yagi, K. Fukumoto, J. Chem. Soc. C 1969, 1063-1065;
15. c) T. Kametani, M. Koizumi, K. Fukumoto, Chem. Pharm. Bull. 1969, 17, 2245-2249;
16. d) T. Kametani, T. Sugahara, H. Yagi, K. Fukumoto, J. Chem. Soc. C 1970, 624-627.
17. a) T. Kametani, K. Fukumoto, Acc. Chem. Res. 1972, 5, 212-219;
18. b) T. Kametani, R. Charubala, M. Ihara, M. Koizumi, K. Takahashi, K. Fukumoto, J. Chem. Soc. C 1971, 3315-3318;
19. c) S. Gupta, D. S. Bhakuni, Synth. Commun. 1988, 18, 2251-2258.
20. a) T. Kametani, S. Shibuya, K. Kigasawa, M. Hiiragi, O. Kusama, J. Chem. Soc. C 1971, 2712-2714;
21. b) T. Kametani, A. Ujiie, K. Takahashi, T. Nakano, T. Suzuki, K. Fukumoto, Chem. Pharm. Bull. 1973, 21, 766-769;
22. b) S. V. Kessar, R. Randhawa, S. S. Gandhi, Tetrahedron Lett. 1973, 14, 2923-2926.
23. a) L. L. Miller, F. R. Stermitz, J. R. Falck, J. Am. Chem. Soc. 1971, 93, 5941-5342;
24. b) L. L. Miller, F. R. Stermitz, J. R. Falck, J. Am. Chem. Soc. 1973, 95, 2651-2656;
25. c) E. Kotani, S. Tobinaga, Tetrahedron Lett. 1974, 15, 931-934;
26. d) H. Klünenberg, C. Schäffer, H.-J. Schäfer, Tetrahedron Lett. 1982, 23, 4581-4584;
27. e) T. W. Bentley, S. J. Morris, J. Org. Chem. 1986, 51, 5005-5007.
28. S. Tobinaga, Bioorg. Chem. 1975, 4, 110-125.
29. a) S. M. Kupchan, A. J. Liepa, V. Kameswaran, R. F. Bryan, J. Am. Chem. Soc. 1973, 95, 6861-6863;
30. b) S. M. Kupchan, V. Kameswaran, J. T. Lynn, D. K. Williams, A. J. Liepa, J. Am. Chem. Soc. 1975, 97, 5622-5623.
31. a) S. M. Kupchan, O. P. Dhingra, C.-K. Kim, V. Kameswaran, J. Org. Chem. 1978, 43, 2521-2529;
32. b) E. C. Taylor, J. G. Andrade, G. J. H. Rall, A. McKillop, J. Am. Chem. Soc. 1980, 102, 6513-6519;
33. c) Y. Landais, D. Rambault, J. P. Robin, Tetrahedron Lett. 1987, 28, 543-546;
34. d) L. Gottlieb, A. I. Meyers, J. Org. Chem. 1990, 55, 5659-5662;
35. e) Y. Landais, J.-P. Robin, Tetrahedron 1992, 48, 7185-7196;
36. f) D. Planchenault, R. Dhal, J.-P. Robin, Tetrahedron 1993, 49, 5823-5830.
37. For reviews, see: a) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178; b) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, 1997; c) T. Kitamura, Y. Fujikawa, Org. Prep. Proced. Int. 1997, 29, 409-458; d) T. Wirth, U. H. Hirt, Synthesis 1999, 1271-1287; e) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523-2584; f) T. Wirth, Hypervalent Iodine in Chemistry, Springer, Berlin, 2003.
38. For reviews, see: a) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178; b) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, 1997; c) T. Kitamura, Y. Fujikawa, Org. Prep. Proced. Int. 1997, 29, 409-458; d) T. Wirth, U. H. Hirt, Synthesis 1999, 1271-1287; e) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523-2584; f) T. Wirth, Hypervalent Iodine in Chemistry, Springer, Berlin, 2003.
39. For reviews, see: a) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178; b) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, 1997; c) T. Kitamura, Y. Fujikawa, Org. Prep. Proced. Int. 1997, 29, 409-458; d) T. Wirth, U. H. Hirt, Synthesis 1999, 1271-1287; e) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523-2584; f) T. Wirth, Hypervalent Iodine in Chemistry, Springer, Berlin, 2003.
40. For reviews, see: a) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178; b) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, 1997; c) T. Kitamura, Y. Fujikawa, Org. Prep. Proced. Int. 1997, 29, 409-458; d) T. Wirth, U. H. Hirt, Synthesis 1999, 1271-1287; e) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523-2584; f) T. Wirth, Hypervalent Iodine in Chemistry, Springer, Berlin, 2003.
41. For reviews, see: a) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178; b) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, 1997; c) T. Kitamura, Y. Fujikawa, Org. Prep. Proced. Int. 1997, 29, 409-458; d) T. Wirth, U. H. Hirt, Synthesis 1999, 1271-1287; e) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523-2584; f) T. Wirth, Hypervalent Iodine in Chemistry, Springer, Berlin, 2003.
42. For reviews, see: a) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178; b) A. Varvoglis, Hypervalent Iodine in Organic Synthesis, Academic Press, San Diego, 1997; c) T. Kitamura, Y. Fujikawa, Org. Prep. Proced. Int. 1997, 29, 409-458; d) T. Wirth, U. H. Hirt, Synthesis 1999, 1271-1287; e) V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523-2584; f) T. Wirth, Hypervalent Iodine in Chemistry, Springer, Berlin, 2003.
43. a) Y. Kita, H. Tohma, K. Hatanaka, T. Takada, S. Fujita, S. Mitoh, H. Sakurai, S. Oka, J. Am. Chem. Soc. 1994, 116, 3684-3691;
44. b) Y. Kita, T. Takada, S. Mihara, H. Tohma, Synlett 1995, 211-212;
45. c) Y. Kita, M. Gyoten, M. Ohtsubo, H. Tohma, T. Takada, Chem. Commun. 1996, 1481-1482;
46. d) Y. Kita, M. Egi, A. Okajima, M. Ohtsubo, T. Takada, H. Tohma, Chem. Commun. 1996, 1491-1492;
47. e) Y. Kita, M. Egi, M. Ohtsubo, T. Saiki, T. Takada, H. Tohma, Chem. Commun. 1996, 2225-2226;
48. f) T. Takada, M. Arisawa, M. Gyoten, R. Hamada, H. Tohma, Y. Kita, J. Org. Chem. 1998, 63, 7698-7706;
49. g) H. Tohma, H. Morioka, S. Takizawa, M. Arisawa, Y. Kita, Tetrahedron 2001, 57, 345-352.
50. a) H. Hamamoto, G. Anilkmar, H. Tohma, Y. Kita, Chem. Commun. 2002, 450-451;
51. b) H. Hamamoto, G. Anilkmar, H. Tohma, Y. Kita, Chem. Eur. J. 2002, 8, 5377-5383.
52. For recent reviews on heteropoly acids, see: a) I. V. Kozhevnikov, Chem. Rev. 1998, 98, 171-198; b) N. Mizuno, M. Misono, Chem. Rev. 1998, 98, 199-217.
53. For recent reviews on heteropoly acids, see: a) I. V. Kozhevnikov, Chem. Rev. 1998, 98, 171-198; b) N. Mizuno, M. Misono, Chem. Rev. 1998, 98, 199-217.
54. 2O is the most efficient acid additive for this reaction.
55. I. V. Kozhevnikov, K. R. Kloetstra, A. Sinnema, H. W. Zandbergen, H. van Bekkum, J. Mol. Catal. A.: Chem. 1996, 114, 287-298.
56. Y. Izumi, K. Matsuo, K. Urabe, J. Mol. Catal. 1983, 18, 299-314.
57. S. M. Kupchan, C.-K. Kim, J. Org. Chem. 1976, 41, 3210-3212.
58. a) T. Kametani, K. Fukumoto, F. Satoh, H. Yagi, J. Chem. Soc. C 1968, 3084-3088;
59. b) B. Gregson-Allcott, J. M. Osbond, Tetrahedron Lett. 1969, 10, 1771-1774;
60. c) S. Dvorackova, L. Hruban, V. Preininger, F. Santavy, Heterocycles 1975, 3, 575-613;
61. d) D. S. Bhakuni, A. N. Singh, Tetrahedron 1979, 35, 2365-2367.
62. S. M. Kupchan, O. P. Dhingra, C.-K. Kim, J. Org. Chem. 1978, 43, 4076-4081.
63. H. Hara, S. Komoriya, T. Miyashita, O. Hoshino, Tetrahedron: Asymmetry 1995, 6, 1683-1692.
64. E. Kotani, S. Tobinaga, Tetrahedron Lett. 1973, 14, 4759-1774.
65. D. L. Comins, P. M. Thakker, M. F. Baevsky, Tetrahedron 1997, 53, 16372-16340.
66. S. M. Kupchan, O. P. Dhingra, C.-K. Kim, J. Org. Chem. 1976, 41, 4049-4050.
67. T. Kametani, K. Takahashi, T. Honda, M. Ihara, K. Fukumoto, Chem. Pharm. Bull. 1972, 20, 1793-1798.