“Naked Sugars” as Synthetic Intermediates. Total Synthesis of L-Daunosamine

Journal of Organic Chemistry

Volumn 51, Issue 26, 1986, Pages 5348-5353

  Warm, Aleksander ^a   Vogel, Pierre ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000164611     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00376a055     Document Type: Article

References (102)

1. Carrupt, P.-A.; Vogel, P. Tetrahedron Lett. 1979, 4533–4536.
2. Tamariz, J.; Vogel, P. Tetrahedron 1984, 40, 4549–4560.
3. Tornare, J.-M.; Vogel, P. Helv. Chim. Acta 1985, 68, 1069–1077.
4. Keay, B. A.; Rodrigo, R. Can. J. Chem. 1983, 61, 637–639.
5. Wiersum, U. E. Aldrichimica Acta 1981, 14, 53.
6. Just, G.; Lim, M. I. Can J. Chem. 1977, 55, 2993–2997.
7. Just, G.; Liak, T. J.; Lim, M. I.; Potvin, P.; Tsantrizos, Y. S. Chem., 1980, 58, 2024–2033.
8. Just, G.; Martel, A. Tetrahedron Lett. 1973, 14, 1517–1520.
9. Kozikowski, A. P.; Floyd, W. C.; Kuniak, M. P. J. Chem. Soc., Chem. Commun. 1977, 582–583.
10. Ito, Y.; Shibata, T.; Arita, M.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 6739–6741.
11. Kozikowski, A. P.; Ames, A. J. Am. Chem. Soc., 1981, 103, 3923–3924.
12. Nelson, W. L.; Allen, D. R.; Vincenzi, F. F. J. Med. Chem. 1971, 14, 698–702.
13. Kotsuki, H.; Nishizana, H. Heterocycles 1981, 16, 1287.
14. Cowling, A. P.; Mann, J.; Usmani, A. A. J. Chem. Soc., Perkin Trans. 1 1981, 2116–2119.
15. Eggelte, T. A.; de Koning, H.; Huisman, H. O. J. Chem. Soc., Perkin Trans. 1 1978, 980–989.
16. Ogawa, S., Iwasawa, Y.; Nose, T.; Suami, T.; Ohba, S.; Ito, M.; Saito, Y. J. Chem. Soc., Perkin Trans. 1 1985, 903–906.
17. Ogawa, S.; Takagaki, T. J. Org. Chem. 1985, 50, 2356–2539.
18. Campbell, M. M.; Kaye, A. D.; Sainsbury, M.; Yavarzadeh, R. Tetrahedron Lett. 1984, 25, 1629–1630.
19. van Royen, L. A.; Mijngheer, R.; De Clerq, P. J. Tetrahedron Lett., 1983, 24, 3145–3148.
20. Holmes, A. B.; Jennings-White, C. L. D.; Kendrick, D. A. J. Chem. Soc., Chem. Commun. 1983, 415–417.
21. Imagawa, T.; Sugita, S.; Akiyama, T.; Kawanisi, M. Tetrahedron Lett. 1981, 22, 2569–2572.
22. Akiyama, T.; Fujii, T.; Ishiwari, H.; Imagawa, T.; Kawanisi, M. Tetrahedron Lett., 1978, 19, 2165–2168.
23. Murai, A.; Takahashi, K.; Taketsuru, H.; Masamune, T. J. Chem. Soc., Chem. Commun. 1981, 221–222.
24. Imagawa, T.; Nakagawa, I.; Matsuura, K.; Akiyama, T.; Kawanisi, M. Chem. Lett. 1981, 903–904.
25. Mukaiyama, T.; Iwasawa, N.; Tsuji, T.; Narasaka, K. Chem. Lett., 1979, 1175.
26. Grieco, P. A.; Zelle, R. E.; Lis, R.; Finn, J. J. Am. Chem. Soc. 1983, 105, 1403–1404, and references cited therein.
27. Chen, R.-T.; Hua, Z.; Yang, J.-L.; Han, J.-X.; Zhang, S.-T.; Lu, F.-L.; Xu, B. Chin. Med. J. (Beijing, Engl. Ed.) 1980, 93, 183.
28. Wang, Z.; Leng, H.; Sha, K.; Liu, J. Fenzi Kexue Yu Huaxue Yanjin 1983, 3, 25;
29. Chem. Abstr. 1984, 100, 17225h.
30. Anderson, W. K.; Dewey, R. H.; Mulumba, B. J. Med. Chem. 1979, 22, 1270–1272.
31. Anderson, W. K.; Dewey, R. H. J. Med. Chem., 1977, 20, 306–308.
32. Fryer, R. I.; Boris, A.; Earley, J. V.; Reeder, E. J. Med. Chem. 1977, 20, 1268–1272.
33. Vieira, E.; Vogel, P. Helv. Chim. Acta 1983, 66, 1865–1871.
34. Black, K. A.; Vogel, P. Helv. Chim. Acta. 1984, 67, 1612–1615.
35. Black, K. A.; Vogel, P. J. Org. Chem., previous paper in this issue.
36. Arcamone, F.; Cassinelli, G.; Orezzi, P.; Franceschi, G.; Mondelli, R. J. Am. Chem. Soc. 1964, 86, 5335–5336.
37. Carter, S. K. J. Natl. Cancer Inst. 1975, 55, 1265.
38. Skovsgaard, T.; Nissen, N. I. Dan. Med. Bull. 1975, 22, 62.
39. Arcamone, F. Med. Res. Rev. 1984, 4, 153.
40. DiMarco, A.; Gaetani, M.; Scarpino, B. Cancer Chemother. Rep. 1969, 53, 33.
41. Richardson, A. C. J. Chem. Soc., Chem. Commun. 1965, 627–628.
42. Richardson, A. C. Carbohydr. Res. 1967, 4, 422.
43. Marsh, J. P.; Mosher, C. W.; Acton, E. M.; Goodman, L. J. Chem. Soc., Chem. Commun. 1967, 973–975.
44. Horton, D.; Weckerle, W. Carbohydr. Res. 1975, 44, 227–240.
45. Yamaguchi, T.; Kojima, M. Carbohydr. Res., 1977, 59, 343–350.
46. Medgyes, G.; Kuszmann, J. Carbohydr. Res., 1981, 92, 225–237.
47. Grethe, G.; Mitt, T.; Williams, T. H.; Uskokovic, M. R. J. Org. Chem. 1983, 48, 5309–5315.
48. Baer, H. H.; Capek, K.; Cook, M. C. Can. J. Chem. 1969, 47, 89–97.
49. Crugnola, A.; Lombardi, P.; Gandolfi, C.; Arcamone, F. Gazz. Chim. Ital. 1981, 111, 395–399.
50. Pauls, H. W.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1983, 1031–1032.
51. Hirama, M.; Nishizaki, I.; Shigemoto, T.; Ito, S. J. Chem. Soc., Chem. Commun., 1986, 393–394.
52. Picq, D.; Carret, G.; Anker, D.; Abou-Assali, M. Tetrahedron Lett. 1985, 26, 1863–1866.
53. Pelyvas, I.; Hasegowa, A.; Whistler, R. L. Carbohydr. Res. 1986, 146, 193–203.
54. Machado, A. S.; Olesker, A.; Castillon, S.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1985, 330–332.
55. Iwataki, I.; Nakamura, Y.; Takahashi, K.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1979, 52, 2731–2732.
56. Fronza, G.; Fuganti, C.; Grasselli, P. J. Chem. Soc., Chem. Commun. 1980, 442–444.
57. Dyong, I.; Wiemann, R. Chem. Ber. 1980, 113, 2666–2674.
58. Dyong, I.; Friege, H.; Zu Hone, T. Chem. Ber., 1982, 115, 256–260.
59. Wovkulich, P. M.; Uskokovic, M. R. J. Am. Chem. Soc. 1981, 103, 3956–3958.
60. Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Org. Chem. 1983, 48, 909–910.
61. Grethe, G.; Sereno, J.; Williams, T. H.; Uskokovic, M. R. J. Org. Chem., 1983, 48, 5315–5317.
62. Hauser F. M.; Rhee, R. P.; Ellenberger, S. R. J. Org. Chem., 1984, 49, 2236–2240.
63. Hauser, F. M.; Ellenberger, S. R.; Glusker, J. P.; Smart, C. J.; Carrell, H. L. J. Org. Chem., 1986, 51, 50–57.
64. DeShong, P.; Leginus, J. M. J. Am. Chem. Soc. 1983, 105, 1686–1688.
65. Mukaiyama, T.; Goto, Y.; Shoda, S. Chem. Lett. 1983, 671–678.
66. Hiyama, T.; Nishide, K.; Kobayashi, K. Chem. Lett., 1984, 361–362.
67. Hamada, Y.; Kawai, A.; Shioiri, T. Chem. Lett., 1984, 25, 5409–5412.
68. Hanessian, S.; Kloss, J. Chem. Lett., 1985, 26, 1261–1264.
69. Sammes, P. G.; Thetford, D. J. Chem. Soc., Chem. Commun. 1985, 352–353.
70. DeShong, P.; Dicken, C. M.; Leginus, J. M.; Whittle, R. R. J. Am. Chem. Soc. 1984, 106, 5598–5602.
71. Danishefsky, S. J.; Maring, C. J. J. Am. Chem. Soc., 1985, 107, 1269–1274.
72. Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron 1985, 41, 3455–3462.
73. Monneret, C.; Coureur, C.; Khuong, H. Q. Carbohydr. Res. 1978, 65, 35.
74. Sharpless, K. B.; Young, M. W.; Lauer, R. F. Tetrahedron Lett. 1973, 1979–1982.
75. Thiele, J. Liebigs Ann. Chem. 1892, 271, 127.
76. Hamersma, J. W.; Snyder, E. I. J. Org. Chem. 1965, 30, 3985–3988.
77. Adam, W.; Eggelte, H. J. Angew. Chem., Int. Ed. Engl. 1978, 17, 765.
78. Baird, W. C., Jr.; Franzus, B.; Surridge, J. H. J. Am. Chem. Soc. 1967, 89, 410.
79. Mazur, Y.; Sondheimer, F. J. Am. Chem. Soc. 1958, 80, 5220–5229.
80. Lukes, R. M.; Poos, G. I.; Beyler, R. E.; Johns, W. F.; Sarett, L. H. J. Am. Chem. Soc., 1953, 75, 1707–1712.
81. Corey, E. J.; Hartmann, R.; Vatakencherry, P. A. J. Am. Chem. Soc., 1962, 84, 2611–2614.
82. Diels, O.; Alder, K. Liebigs Ann. Chem. 1931, 486, 202–210.
83. Meinwald, J.; Frauenglass, E. J. Am. Chem. Soc. 1960, 82, 5235–5239.
84. Schmidt, R. R.; Beitzke, C.H.; Forrest, A. K. J. Chem. Soc., Chem. Commun. 1982, 909–910.
85. Loev, B. Chem. Ind. (London) 1964, 193.
86. Jorgenson, M. J. Org. React. (N.Y.) 1970, 18, 1–97.
87. DePuy, C. H.; Dappen, G. M.; Eilers, K. L.; Klein, R. A. J. Org. Chem. 1964, 29, 2813–2815.
88. Bare, T. M.; House, H. O. Org. Synth. 1969, 49, 81.
89. Emmons, W. D.; Lucas, G. B. J. Am. Chem. Soc. 1955, 77, 2287–2288.
90. Sheldon, R. A.; Kochi, J. K. Org. React. (N.Y.) 1972, 19, 279–421.
91. Malik, A.; Afza, N.; Voelter, W. J. Chem. Soc., Perkin Trans. 1 1983, 2103–2109.
92. Horton, D.; Wander, J. D. In Amino Sugars, Carbohydr.: Chem., Biochem., 2nd ed.; Pigman, W. W., Horton, D., J.,; Academic Press: New York, 1980.
93. Nayak, U. G.; Whistler, R. L. J. Org. Chem. 1969, 34, 3819–3822. Reference 15e.
94. Moore, A. T.; Rydon, H. N. Org. Synth. (N.Y.) 1965, 45, 47–49. See also ref 15b,e,f.
95. Kuivila, H. G. Acc. Chem. Res. 1968, 1, 299–305.
96. Menapace, L. W.; Kuivila, H. G. J. Am. Chem. Soc. 1964, 86, 3047–3051.
97. Gutierrez, C. G.; Summerhays, L. R. J. Org. Chem. 1984, 49, 5206–5213.
98. Pang, M.; Becker, E. I. J. Org. Chem., 1964, 29, 1948–1952.
99. Haskell, T. H.; Woo, P. W. K.; Watson, D. R. J. Org. Chem., 1977, 42, 1302–1305.
100. Pettit, G. R.; van Tamelen, E. E. Org. React. (N.Y.) 1962, 12, 356.
101. Berson, J. A.; Jones, W. M. J. Am. Chem. Soc. 1956, 78, 6045–6048.
102. Stork, G.; van Tamelen, E. E.; Friedman, L. J.; Burgstahler, A. W. J. Am. Chem. Soc., 1953, 75, 384–392.