Total syntheses of bioactive natural products from carbohydrates

References

• K. Tatsuta, S. Hosokawa, Chem. Rev. 105 (2005) 4707.
   Google Scholar
• K. Tatsuta, Adv. Synth. Catal. 343 (2001) 143.
   Google Scholar
• K. Tatsuta, Curr. Org. Chem. 5 (2001) 207.
   Google Scholar
• K. Toshima, K. Tatsuta, Chem. Rev. 93 (1993) 1503.
   Google Scholar
• S. Ōmura, H. Tanaka, Y. Koyama, R. Ōiwa, M. Katagiri, J. Awaya, T. Nagai, T. Hata, J. Antibiot. 27 (1974) 363.
   Google Scholar
• H. Tanaka, Y. Koyama, T. Nagai, H. Marumo, S. Ōmura, J. Antibiot. 28 (1975) 868.
   Google Scholar
• H.W. Moore, 197 (1977) 527.
   Google Scholar
• S. Ōmura, H. Tanaka, Y. Okada, H. Marumo, J. Chem. Soc. Chem. Commun. (1976) 320.
   Google Scholar
• M.E. Bergy, J. Antibiot. 21 (1968) 454.
   Google Scholar
• H. Hoeksema, W.C. Krueger, J. Antibiot. 29 (1976) 704.
   Google Scholar
• M. Tsukamoto, S. Nakajima, K. Murooka, M. Hirayama, K. Hirano, S. Yoshida, K. Kojiri, H. Suda, J. Antibiot. 53 (2000) 26.
   Google Scholar
• K. Tatsuta, K. Akimoto, M. Annaka, Y. Ohno, M. Kinoshita, Bull. Chem. Soc. Jpn 58 (1985) 1699.
   Google Scholar
• K. Tatsuta, K. Akimoto, M. Annaka, Y. Ohno, M. Kinoshita, J. Antibiot. 38 (1985) 680.
   Google Scholar
• K. Tatsuta, H. Ozeki, M. Yamaguchi, M. Tanaka, T. Okui, Tetrahedron Lett. 31 (1990) 5495.
   Google Scholar
• K. Tatsuta, H. Ozeki, M. Yamaguchi, M. Tanaka, T. Okui, M. Nakata, J. Antibiot. 44 (1991) 901.
   Google Scholar
• T. -T. Li, R.H. Ellison, J. Am. Chem. Soc. 100 (1978) 6263.
   Google Scholar
• Y. Naruta, K. Maruyama, J. Synth. Org. Chem. Jpn 42 (1984) 415.
   Google Scholar
• M.P. Winters, M. Stranberg, H.W. Moore, J. Org. Chem. 59 (1994) 7572.
   Google Scholar
• R.A. Fernandes, R. Bruckner, Synlett (2005) 1281.
   Google Scholar
• M.S. South, L.S. Liebeskind, J. Am. Chem. Soc. 106 (1984) 4181 (and references cited therein).
   Google Scholar
• T. Kometani, Y. Takeuchi, E. Yoshii, J. Chem. Soc. Perkin Trans. 1 (1981) 1197.
   Google Scholar
• M.F. Semmelhack, L. Keller, T. Sato, E. Spiess, J. Org. Chem. 47 (1982) 4382.
   Google Scholar
• M.F. Semmelhack, J.J. Bozell, T. Sato, W. Wulff, E. Spiess, A. Zask, J. Am. Chem. Soc. 104 (1982) 5850.
   Google Scholar
• M.F. Semmelhack, A. Zask, J. Am. Chem. Soc. 105 (1983) 2034.
   Google Scholar
• P.A. Bartlett, J.D. Meadows, E. Ottow, J. Am. Chem. Soc. 106 (1984) 5304.
   Google Scholar
• B.M. Trost, J.M. Timko, J.L. Stanton, J. Chem. Soc., Chem. Commun. (1978) 436.
   Google Scholar
• J. -F. Zheng, L. -R. Jin, P. -Q. Huang, Org. Lett. 6 (2004) 1139.
   Google Scholar
• A. Jirgensons, M. Marinozzi, R. Pellicciari, Tetrahedron 61 (2005) 373.
   Google Scholar
• A.S. Kirrev, A.T. Breithaupt, W. Collins, O.N. Nadein, A. Kornienko, J. Org. Chem. 70 (2005) 742.
   Google Scholar
• N.K. Greg, D.D. Caspi, B.M. Stoltz, J. Am. Chem. Soc. 127 (2005) 5970.
   Google Scholar
• F. Cardona, E. Faggi, F. Liguori, M. Cacciarini, A. Goti, Tetrahedron Lett. 44 (2003) 2315.
   Google Scholar
• J. Zhu, D. Ma, Angew. Chem. Int. Ed. Engl. 42 (2004) 5348.
   Google Scholar
• F.W. Lichtenthaler, K. Nakamura, J. Klotz, Angew. Chem. Int. Ed. Engl. 42 (2004) 5838.
   Google Scholar
• K. Totani, K. Takao, K. Tadano, Synlett (2004) 2061.
   Google Scholar
• M. Bohno, H. Imase, N. Chida, Chem. Commun. (2004) 1086.
   Google Scholar
• L.A. Paquette, Y. Zhang, Org. Lett. 7 (2005) 511.
   Google Scholar
• B. Szechner, O. Achmatowicz, J.-K. Maunin, Tetrahedron 61 (2005) 1981.
   Google Scholar
• T. Tatsuta, K. Akimoto, M. Kinoshita, J. Am. Chem. Soc. 101 (1979) 6116.
   Google Scholar
• K. Tatsuta, K. Akimoto, M. Kinoshita, J. Antibiot. 33 (1980) 100.
   Google Scholar
• K. Tatsuta, K. Akimoto, M. Kinoshita, Tetrahedron 37 (1981) 4365.
   Google Scholar
• F.M. Hauser, D. Mal, J. Am. Chem. Soc. 106 (1984) 1098.
   Google Scholar
• F.M. Hauser, D. Mal, J. Am. Chem. Soc. 106 (1984) 1862.
   Google Scholar
• K. Tatsuta, J. Synth. Org. Chem. Jpn 42 (1984) 497.
   Google Scholar
• R.D. Dawe, B. Fraser-Reid, J. Org. Chem. 49 (1984) 522.
   Google Scholar
• K. Tatsuta, T. Hirabayashi, M. Kojima, Y. Suzuki, T. Ogura, J. Antibiot. 57 (2004) 291.
   Google Scholar
• R.B. Woodward, Pure Appl. Chem. 6 (1963) 561.
   Google Scholar
• L.H. Conover, K. Butler, J.D. Johnston, J.J. Korst, R.B. Wood- ward, J. Am. Chem. Soc. 84 (1962) 3222.
   Google Scholar
• H. Muxfeldt, G. Hardtmann, F. Kathawala, E. Vedejs, J.B. Mooberry, J. Am. Chem. Soc. 90 (1968) 6534.
   Google Scholar
• G. Stork, J.J. La Clair, P. Spargo, R.P. Nargund, N. Totah, J. Am. Chem. Soc. 118 (1996) 5304 (and references cited therein).
   Google Scholar
• K. Tatsuta, T. Yoshimoto, H. Gunji, Y. Okado, M. Takahashi, Chem. Lett. (2000) 646.
   Google Scholar
• M.G. Charest, D.R. Siegel, A.G. Myers, J. Am. Chem. Soc. 127 (2005) 8292.
   Google Scholar
• M.G. Charest, C.D. Lerner, J.D. Brubaker, D.R. Siegel, A.G. Myers, Science 308 (2005) 395.
   Google Scholar
• J. -C. Jacquinet, M. Petitou, P. Duchaussoy, I. Lederman, J. Choay, G. Torri, P. Sinay, Carbohydr. Res. 130 (1984) 221.
   Google Scholar
• P.A. Grieco, S. Gilman, M. Nishizawa, J. Org. Chem. 41 (1976) 1485 (and references cited therein).
   Google Scholar
• R.J. Ferrier, Chem. Soc. Perkin Trans. 1 (1979) 1455.
   Google Scholar
• R. Gleiter, M.C. Böhm, Pure Appl. Chem. 55 (1983) 237.
   Google Scholar
• S. Kushner, J.H. Boothe, J. Morton, J. Petisi, J.H. Williams, J. Am. Chem. Soc. 74 (1952) 3710.
   Google Scholar
• S. Hanessian, Organic Chemistry Series: Total Synthesis of Natural Products: The “Chiron” Approach, vol. 3, Pergamon, Oxford, UK, 1983.
   Google Scholar
• S. Kondo, S. Shibahara, S. Takahashi, K. Maeda, H. Umezawa, J. Am. Chem. Soc. 93 (1971) 6305.
   Google Scholar
• K. Tatsuta, S. Miyashita, K. Akimoto, M. Kinoshita, Bull. Chem. Soc. Jpn 55 (1982) 3254.
   Google Scholar
• K. Tatsuta, H. Takahashi, Y. Amemiya, M. Kinoshita, J. Am. Chem. Soc. 105 (1983) 4096.
   Google Scholar
• L.A. Porter, T.A. Geissman, J. Org. Chem. 27 (1962) 4132.
   Google Scholar
• M.F. Richardson, F.L. Warren, J. Chem. Soc. (1943) 452.
   Google Scholar
• A. Goti, M. Cacciarini, F. Cardona, F.M. Cordero, A. Brandi, Org. Lett. 3 (2001) 1367.
   Google Scholar
• S.E. Denmark, A. Thorarensen, D.S. Middleton, J. Am. Chem. Soc. 118 (1996) 8266.
   Google Scholar
• M. Kinoshita, N. Ohsawa, S. Gomi, Carbohydr. Res. 109 (1982) 5.
   Google Scholar
• Y. Tsuda, T. Nunozawa, K. Yoshimoto, Chem. Pharm. Bull. 28 (1980) 3223.
   Google Scholar
• J.S. Kahan, F.M. Kahan, R. Goegelman, S.A. Currie, M. Jackson, E.O. Stapley, T.W. Miller, A.K. Miller, D. Hendlin, S. Mochales, S. Hernandez, H.B. Woodruff, J. Birnbaum, J. Antibiot. 32 (1979) 1.
   Google Scholar
• T.N. Salzmann, R.W. Ratcliffe, B.G. Christensen, F.A. Bouffard, J. Am. Chem. Soc. 102 (1980) 6161.
   Google Scholar
• P.J. Reider, E.J.J. Grabowski, Tetrahedron Lett. 23 (1982) 2293.
   Google Scholar
• A.H. Berks, Tetrahedron 52 (1996) 331.
   Google Scholar
• M. Sunagawa, H. Matsunuma, T. Inoue, M. Fukasawa, M. Kato, J. Antibiot. 43 (1990) 519.
   Google Scholar
• A. Yoshida, T. Hayashi, N. Takeda, S. Oida, E. Ohki, Chem. Pharm. Bull. 29 (1981) 2899.
   Google Scholar
• W.J. Leanza, F. DiNinno, D.A. Muthard, R.R. Wilkening, K.J. Wildonger, R.W. Ratcliffe, B.G. Christensen, Tetrahedron 39 (1983) 2505.
   Google Scholar
• H. Kumobayashi, T. Miura, N. Sayo, T. Saito, J. Synth. Org. Chem. Jpn 57 (1999) 387.
   Google Scholar
• T. Ohashi, K. Kan, I. Sada, A. Miyama, K. Watanabe, Eur. Pat. Appl. Ep. 167, 154 (1986).
   Google Scholar
• K. Tatsuta, M. Takahashi, N. Tanaka, K. Chikauchi, J. Antibiot. 53 (2000) 1231.
   Google Scholar
• E.J. Smith, Biochem. Biophys. Res. Commun. 15 (1964) 593.
   Google Scholar
• G. Sedelmeier, J. Bersier, Eur. Pat. Appl. Ep. 279, 781 (1988).
   Google Scholar
• L. Birkofer, J. Schramm, Liebigs Ann. Chem. (1975) 2195.
   Google Scholar
• N. Naruse, R. Kageyama-Kawase, Y. Funahashi, T. Wakabayashi, Y. Watanabe, T. Sameshima, K. Dobashi, J. Antibiot. 53 (2000) 579.
   Google Scholar
• T. Tamaoki, K. Sugawara, M. Hamada, H. Nakano, T. Mizukami, Y. Yamashita, N. Kosaka, T. Sugawara, Jpn Kokai Tokkyo Koho 268 (1996) 888.
   Google Scholar
• S.V. Sharma, C. Oneyama, Y. Yamashita, H. Nakano, K. Sugawara, M. Hamada, N. Kosaka, T. Tamaoki, Oncogene 20 (2001) 2068.
   Google Scholar
• K. Tatsuta, S. Nakano, F. Narazaki, Y. Nakamura, Tetrahedron Lett. 42 (2001) 7625.
   Google Scholar
• B.M. Kim, K.B. Sharpless, Tetrahedron Lett. 30 (1989) 655.
   Google Scholar
• T. Tsuchida, R. Sawa, H. Inuma, C. Nishida, N. Kinoshita, Y. Takahashi, H. Naganawa, T. Sawa, M. Hamada, T. Takeuchi, J. Antibiot. 47 (1994) 386.
   Google Scholar
• T. Tsuchida, H. Inuma, C. Nishida, N. Kinoshita, T. Sawa, M. Hamada, T. Takeuchi, J. Antibiot. 48 (1995) 1104.
   Google Scholar
• T. Tsuchida, H. Inuma, R. Sawa, Y. Takahashi, H. Nakamura, K.T. Nakamura, T. Sawa, H. Naganawa, T. Takeuchi, J. Antibiot. 48 (1995) 1110.
   Google Scholar
• The carbon-numbering protocol parallels conveniently that of the natural product 68 as references 86 and 88.
   Google Scholar
• T. Tsuchida, H. Inuma, K.T. Nakamura, H. Nakamura, T. Sawa, M. Hamada, T. Takeuchi, J. Antibiot. 48 (1995) 1330.
   Google Scholar
• F.F. Paintner, L. Allmendinger, G. Bauschke, C. Berns, P. Heisig, Bioorg. Med. Chem. 11 (2003) 2823.
   Google Scholar
• F.F. Paintner, G. Bauschke, K. Polborn, Tetrahedron Lett. 44 (2003) 2549.
   Google Scholar
• F.F. Paintner, L. Allmendinger, G. Bauschke, K. Polborn, Synlett (2002) 1308.
   Google Scholar
• J.M. Warrington, L. Barriault, Org. Lett. 7 (2005) 4589.
   Google Scholar
• L. Barriault, I. Denissova, Org. Lett. 4 (2002) 1371.
   Google Scholar
• K. Tatsuta, Y. Suzuki, A. Furuyama, H. Ikegami, Tetrahedron Lett. (in press).
   Google Scholar
• K. Tatsuta, F. Narazaki, N. Kashiki, J. Yamamoto, S. Nakano, J. Antibiot. 56 (2003) 584.
   Google Scholar
• F. Matsuda, J. Synth, Org. Chem. Jpn 53 (1995) 987.
   Google Scholar
• D. Basavaiah, A.J. Rao, T. Satyanarayana, Chem. Rev. 103 (2003) 811.
   Google Scholar
• T. Fukuyama, S.-C. Lin, L. Li, J. Am. Chem. Soc. 112 (1990) 7050.
   Google Scholar
• L.A. Jones, C.E. Sumner Jr., B. Franzus, T.T.-S. Huang, E.I. Snyder, J. Org. Chem. 43 (1978) 2821.
   Google Scholar
• I.J. Borowitz, K.C. Kirby Jr., R. Virkhaus, J. Org. Chem. 31 (1966) 4031.
   Google Scholar
• S. Takano, K. Inomata, K. Samizu, S. Tomita, M. Yanase, M. Suzuki, Y. Iwabuchi, T. Sugihara, K. Ogasawara, Chem. Lett. 18 (1989) 1283.
   Google Scholar
• K. Shindo, H. Kawai, J. Antibiot. 45 (1992) 292.
   Google Scholar
• K. Shindo, H. Iijima, H. Kawai, J. Antibiot. 49 (1996) 244.
   Google Scholar
• J.E. Hochlowski, M.M. Mullally, R. Henry, D.M. Whittern, J.B. McAlpine, J. Antibiot. 48 (1995) 467.
   Google Scholar
• J. Chang, L.A. Paquette, Org. Lett. 4 (2002) 253.
   Google Scholar
• L.A. Paquette, J. Chang, Z. Liu, J. Org. Chem. 69 (2004) 6441.
   Google Scholar
• R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K.-I. Takao, K.-I. Tadano, J. Am. Chem. Soc. 126 (2004) 11245.
   Google Scholar
• R. Munakata, H. Katakai, T. Ueki, J. Kurosaka, K.-I. Takao, K.-I. Tadano, J. Am. Chem. Soc. 125 (2003) 14722.
   Google Scholar
• T.A. Dineen, W.R. Roush, Org. Lett. 6 (2004) 2043.
   Google Scholar
• K. Tatsuta, S. Yasuda, K.-I. Kurihara, K. Tanabe, R. Shinei, T. Okonogi, Tetrahedron Lett. 38 (1997) 1439.
   Google Scholar
• K. Tatsuta, S. Takano, T. Sato, S. Nakano, Chem. Lett. (2001) 172.
   Google Scholar
• T.J. Simpson, R.W. Smith, S.M. Westaway, C.L. Willis, A.D. Buss, R.J.P. Cannell, M.J. Dawson, B.A.M. Rudd, Tetrahedron Lett. 38 (1997) 5367.
   Google Scholar
• K. Takeda, E. Kawanishi, H. Nakamura, E. Yoshii, Tetrahedron Lett. 32 (1991) 4925.
   Google Scholar
• T. Tabuchi, K. Kawamura, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 27 (1986) 3889.
   Google Scholar
• Y. Kita, H. Maeda, K. Omori, T. Okuno, Y. Tamura, J. Chem. Soc. Perkin Trans. 1 (1993) 2999.
   Google Scholar
• M. Igarashi, C. Hayashi, Y. Homma, S. Hattori, N. Kinoshita, M. Hamada, T. Takeuchi, J. Antibiot. 53 (2000) 1096.
   Google Scholar
• M. Igarashi, H. Nakamura, H. Naganawa, T. Takeuchi, J. Antibiot. 53 (2000) 1102.
   Google Scholar
• T. Motozaki, K. Sawamura, A. Suzuki, K. Yoshida, T. Ueki, A. Ohara, R. Munakata, K. Takao, K. Tadano, Org. Lett. 7 (2005) 2261.
   Google Scholar
• T. Motozaki, K. Sawamura, A. Suzuki, K. Yoshida, T. Ueki, A. Ohara, R. Munakata, K. Takao, K. Tadano, Org. Lett. 7 (2005) 2265.
   Google Scholar
• S. Hosokawa, M. Seki, H. Fukuda, K. Tatsuta, Tetrahedron Lett. 47 (2006) 2439.
   Google Scholar
• K. Tatsuta, S. Yasuda, N. Araki, M. Takahashi, Y. Kamiya, Tetrahedron Lett. 39 (1998) 401.
   Google Scholar
• K. Tatsuta, M. Itoh, R. Hirama, N. Araki, M. Kitagawa, Tetrahedron Lett. 38 (1997) 583.
   Google Scholar
• N. Miyaura, A. Suzuki, Chem. Rev. 95 (1995) 2457.
   Google Scholar
• I. Shiina, M. Kubota, R. Ibuka, Tetrahedron Lett. 43 (2002) 7535.
   Google Scholar