Abstract
Synthetic carbohydrate chemistry has undergone a renaissance in the last decade, and the purpose of this chapter is to highlight some of the more significant advances that have taken place in the area. All aspects of the subject are reviewed annually in the Royal Society of Chemistry publication Specialist Periodical Reports: Carbohydrate Chemistry.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
W. Koenigs and E. Knorr, 1901, Ber., 34,957.
P. Brigl, 1922, Z. Physiol Chem., 122, 257.
R. Lemieux and G. Huber, 1953, J. Amer. Chem. Soc., 75, 4118.
R.U. Lemieux, 1964, Chem. in Canada, 14
N.K. Kochetkov, A.J. Khorlin and A.F. Bochkov, 1964, Tetrahedron Lett., 289
N.K. Kochetkov, A.J. Khorlin and A.F. Bochkov, 1967, Tetrahedron, 23, 693
N.K. Kochetkov, A.B. Bochkov, T.A. Sokolovskaya and V.I. Snyatkova, 1971, Carbohydrate Res., 16, 17
A.F. Bochkov and N.K. Kochetkov, 1975, Carbohydrate Res., 39, 355
V.I. Betanelli, M.V. Ovchinnikov, L.V. Backinowsky and N.K. Kochetkov, 1979, Carbohydrate Res., 76, 252.
N.K. Kochetkov, A.F. Bochkov and I.G. Yazlovetsky, 1969, Carbohydrate Res., 9, 49
N.K. Kochetkov and A.F. Bochkov, 1969, Carbohydrate Res., 9, 61.
R.U. Lemieux and B. Fraser-Reid, 1964, Can. J. Chem., 42, 532
R.U. Lemieux and A.R. Morgan, 1965, Can. J. Chem., 43, 2190.
R.U. Lemieux, T.L. Nagabhushan and S.W. Gunner, 1968, Can. J. Chem., 46, 405
R.U. Lemieux, Y. Ito, K. James and T.L. Nagabhushan, 1973, Can. J. Chem., 51, 7
R.U. Lemieux, K. James and T.L. Nagabhushan, 1973, Can. J. Chem., 51, 42, 48.
B. Helferich and E. Schmitz-Hillebrecht, 1933, Ber., 66, 378.
R.J. Ferrier and N. Prasad, 1968, Chem. Comm., 476
R.J. Ferrier and N.K. Prasad, 1969, J. Chem. Soc. (C), 570
A. Canas-Rodriguez and A. Martinez-Tobed, 1979, Carbohydrate Res., 68, 43.
R.J. Ferrier, R.W. Hay and N. Vethaviyasar, 1973, Carbohydrate Res., 27, 55.
J.-R. Pougny and P. Sinay, 1976, Tetrahedron Lett., 4073
J.-R. Pougny, J.C. Jacquinet, M. Nassr, D. Duchet, M.-L. Milat and P. Sinay, 1977, J. Amer. Chem. Soc., 99, 6762
P. Sinay, 1978, Pure and Appl. Chem., 50, 1437.
R.U. Lemieux, K.B. Hendricks, R.V. Stick and K. James, 1975, J. Amer. Chem. Soc., 77, 4056
R.U. Lemieux and H. Driguez, 1975, J. Amer. Chem. Soc., 97, 4063, 4069
R.U. Lemieux, D.R. Bundle and D.A. Baker, 1975, J. Amer. Chem. Soc., 97, 4076.
J. Stanek, M. Cerny and J. Pacak, 1965, The Oligosaccharides, Czechoslovak Academy of Science, Prague
R.J. Ferrier, 1970, Fortschr. Chem. Forsch., 14, 289
N.K. Kochetkov, O.S. Chizov and A.F. Bochkov, 1973, ‘MTP International Review of Science, Organic Chemistry’ Ser. 1, Vol. 7, Ed. G.O. Aspinall, Butterworths, London
G. Wulff and G. Rohle, 1974, Angew. Chem. (Int. Edn.), 13, 157
S. Hanessian and J. Banoub, 1976, Adv. Chem. Ser., 39, 36
K. Igarashi, 1977, Adv. Carbohydrate Chem. Biochem., 34, 243
A.F. Bochkov and G.E. Zaikov, 1979, Chemistry of the O-Glycosidic Bond: Formation and Cleavage, Pergamon Press, Oxford
H. Paulsen, 1982, Angew. Chem. (Int. Edn.), 21, 155
R.H. Khan, J.K. Wold and B.S. Paulsen, Rodd’s Chemistry of Carbon Compounds Supplement to Vol I FG, Ed. M.F. Ansell, 1983, Chapter 24, 231
H. Paulsen, 1984, Chem. Soc. Rev., 13, 15
R.R. Schmidt, 1986, Angew. Chem. (Int. Edn.), 25, 212
H. Kunz, 1987, Angew. Chem. (Int. Edn.), 26, 294
P. Fugedi, P.J. Garregg, H. Lonn and T. Norberg, 1987, Glycoconjugate J., 4, 97
P. Sinay, 1991, Pure and Appl. Chem., 63, 519.
R.U. Lemieux, 1951, Can. J. Chem., 29, 1079.
S. Hanessian and Y. Guindon, 1980, Carbohydrate Res., 86, C3.
K.C. Nicolaou, S.P. Seitz and D.P. Papahatjis, 1983, J. Amer. Chem. Soc., 105, 2430.
R.B. Woodward et al., 1981, J. Amer. Chem. Soc., 103, 3215.
Y. Ito and T. Ogawa, 1988, Tetrahedron Lett., 29, 1061
Y. Ito, T. Ogawa, M. Numata and M. Sugimoto, 1990, Carbohydrate Res., 202, 165.
H. Lonn, 1985, Carbohydrate Res., 139, 105 & 115.
P. Fugedi and P.J. Garegg, 1986, Carbohydrate Res., 149, C9–C12.
F. Dasgupta and P.J. Garegg, 1990, Carbohydrate Res., 202, 225.
Y.D. Vankar, P.S. Vankar, M. Behrendt and R.R. Schmidt, 1991, Tetrahedron, 47, 9985.
C. Amatore, A. Jutand, J.-M. Mallet, G. Meyer and P. Sinay, 1990, J. Chem. Soc. Chem. Comm., 718.
A. Marra, L.K.S. Shun, F. Gauffeny and P. Sinay, 1990, Synlett, 445.
S. Hanessian, C. Bacquet and N. Lehong, 1980, Carbohydrate Res., 80, C17.
G.V. Reddy, V.R. Kulkarni and H.B. Mereyala, 1989, Tetrahedron Lett., 30, 4283
H.B. Mereyala and G.V. Reddy, 1991, Tetrahedron, 47, 9721
H.B. Mereyala, V.R. Kulkarni, D. Ravi, G.V.M. Sharma, B.V. Rao and G.V. Reddy, 1992, Tetrahedron, 48, 545.
K. Tatsuta, Y. Kobayashi, H. Gunji and H. Masuda, 1988, Tetrahedron Lett., 29, 3975.
N.K. Kochetkov, E.M. Klimov and N.N. Malysheva, 1989, Tetrahedron Lett., 30, 5459
N.K. Kochetkov, E.M. Klimov, N.N. Malysheva and A. Demchenko, 1991, Carbohydrate Res., 212, 77.
T. Mukaiyama, Y. Murai and S. Shoda, 1981, Chem. Lett., 431.
K.C. Nicolaou, C.W. Hummel, N.J. Bockovitch and C.H. Wong, 1991, J. Chem. Soc. Chem. Comm., 870.
K.C. Nicolaou, R.E. Dolle, D.P. Papahatjis and J.L. Randall, 1984, J. Amer. Chem. Soc., 106, 4189.
Y. Takahashi and T. Ogawa, 1987, Carbohydrate Res., 164, 277.
S. Hashimoto, M. Hayashi and R. Noyori, 1984, Tetrahedron Lett., 25, 1379.
K.C. Nicolaou, A. Chucholowski, R.E. Dolle and J.L. Randall, 1984, J. Chem. Soc. Chem. Comm., 1155.
H.P. Wessel and N. Ruiz, 1991, J. Carbohydrate Chem., 10, 901.
T. Mukaiyama, Y. Hashimoto and S. Shoda, 1983, Chem. Lett., 935.
F. Micheel and A. Klemer, 1961, Adv. Carbohydrate Chem. Biochem., 16, 85.
A.A.E. Penglis, 1981, Adv. Carbohydrate Chem. Biochem., 38, 195.
P.J. Card, 1985, J. Carbohydrate Chem., 4, 451.
T. Tsuchiya, 1990, Adv. Carbohydrate Chem. Biochem., 48, 91.
S. Caddick, W.B. Motherwell and J.A. Wilkinson, 1991, J. Chem. Soc. Chem. Comm., 674, 1140.
W. Rosenbrook, Jr., D.A. Riley and P.A. Lartey, 1985, Tetrahedron Lett., 26, 3
G.H. Posner and S.R. Haines, 1985, Tetrahedron Lett., 26, 5.
Y. Araki, K. Watanabe, F.-H. Kuan, K. Itoh, N. Kobayashi and Y. Ishido, 1984, Carbohydrate Res., 127, C5
F.H. Kuan, N. Kobayashi, K. Watanabe, K. Itoh, Y. Araki and Y. Ishido, 1985, Nippon Kagaku Kaishi, 2040
Y. Araki, N. Kobayashi, Y. Ishido and I. Nagasawa, 1987, Carbohydrate Res., 171, 125.
H. Kunz and W. Sager, 1985, Helv. Chim. Acta, 68, 283.
T. Mukaiyama, Challenges in Synthetic Organic Chemistry, Oxford University Press, 1990, Chapter 12.
M.N. Sharma and R. Eby, 1984, Carbohydrate Res., 127, 201
M. Hayashi, S. Hashimoto and R. Noyori, 1984, Chem. Lett., 1747
W.A. Szarek, G. Grynkiewicz, B. Doboszewski and W. Hay, 1984, Chem. Lett., 1751
M. Imoto, N. Kusunose, Y. Matsuura, S. Kusumoto and T. Shiba, 1987, Tetrahedron Lett., 28, 6277.
K.C. Nicolaou, T. Ladduwahetty, J.L. Randall and A. Chucholowski, 1986, J. Amer. Chem. Soc., 108, 2466.
S. Mehta and B.M. Pinto, 1991, Tetrahedron Lett., 32, 4435.
R.R. Schmidt and J. Michel, 1985, J. Carbohydrate Chem., 4,141.
B. Wegmann, 1985, Diplomarbeit, Universitat Konstanz.
R.R. Schmidt and J. Michel, 1984, Tetrahedron Lett., 25, 821
R.R. Schmidt, J. Michel and M. Roos, 1984, Liebigs Ann. Chem., 1343.
R.L. Halcomb, S. Boyer and S. Danishefsky, 1992, Angew. Chem. (Int. Edn.), 31, 338.
S. Hashimoto, T. Honda and S. Ikegami, 1989, J. Chem. Soc. Chem. Comm., 685.
A.B. Smith III, K.J. Hale and R.A. Rivero, 1986, Tetrahedron Lett., 27, 5813
A.B. Smith III, R.A. Rivero, K.J. Hale and H.A. Vaccaro, 1991, J. Amer. Chem. Soc., 113, 2092
A.B. Smith III, K.J. Hale, H.A. Vaccaro and R.A. Rivero, 1991, J. Amer. Chem. Soc., 113,2112.
G. Grynkiewicz, 1977, Carbohydrate Res., 53, C11.
W.C. Szarek, H.C. Jarrell and J.K.N. Jones, 1977, Carbohydrate Res., 57, C13
B.R. Castro, 1983, Org. Reactions., 29, 1.
T. Mukaiyama and S. Suda, 1990, Chem. Lett., 1143.
D. Kahne, S. Walker, Y. Cheng and D. Van Engen, 1989, J. Amer. Chem. Soc., 111, 6881.
N. Ikemoto and S.L. Schreiber, 1992, J. Amer. Chem. Soc., 114, 2524.
F. Barresi and O. Hindsgaul, 1991, J. Amer. Chem. Soc., 113, 9376.
G. Stork and G. Kim, 1992, J. Amer. Chem. Soc., 114, 1087.
M. Bols, 1992, J. Chem. Soc Chem. Comm., 913.
A.G.M. Barrett, B.C.B. Bezuidenhoudt and L.M. Melcher, 1990, J. Org. Chem., 55, 5196.
A.G.M. Barrett, B.C.B. Bezuidenhoudt, A.F. Gasiecki, A.R. Howell and M.A. Russell, 1989, J. Amer. Chem. Soc., 111, 1392
A.G.M. Barrett and A.C. Lee, 1992, J. Org. Chem., 57, 2818.
B. Fraser-Reid, P. Konradsson, D.R. Mootoo and U. Udodong, 1988. Â J. Chem. Soc. Chem. Comm., 823
D.R. Mootoo, P. Konradsson, U. Udodong and B. Fraser-Reid, 1988, J. Amer. Chem. Soc., 110, 5583
B. Fraser-Reid, Z. Wu, C.W. Andrews and E. Skowronski, 1991, J. Amer. Chem. Soc., 113, 1434
C.J. Lopez and B. Fraser-Reid, 1992, J. Chem. Soc. Chem. Comm., 94.
P. Konradsson, D.R. Mootoo, R.E. McDevitt and B. Fraser-Reid, 1990, J. Chem. Soc. Chem. Comm., 270.
R.W. Friesen and S.J. Danishefsky, 1989, J. Amer. Chem. Soc., 111, 6656
R.W. Friesen and S.J. Danishefsky, 1990, Tetrahedron, 46, 103
K. Suzuki, G. Sulikowski, R.W. Friesen and S.J. Danishefsky, 1990, J. Amer. Chem. Soc., 112, 8895.
N. Sakairi and H. Kuzuhara, 1992, J. Chem. Soc. Chem. Comm., 510.
J. Thiem, H. Karl and J. Schwenter, 1978, Synthesis, 696
J. Thiem, 1984, Nachr. Chem. Tech. Lab., 32, 6
J. Thiem, 1989, ACS Symp. Ser., 386, 131.
S.J. Danishefsky, D.M. Armistead, F.E. Wincott, H.G. Selnick and R. Hungate, 1989, J. Amer. Chem. Soc., 111, 2967.
D.E. Wright, 1979, Tetrahedron, 35, 1207.
G. Jaurand, J.-M. Beau and P. Sinay, 1981, J. Chem. Soc. Chem. Comm., 572
G. Jaurand, J.-M. Beau and P. Sinay, 1982, J. Chem. Soc Chem. Comm., 701
J.-M. Beau, G. Jaurand, J. Esnault and P. Sinay, 1987, Tetrahedron Lett., 28, 1105
J.-P. Praly, Z. El Kharraf, P.-J. Corringer, L. Brard and G. Descotes, 1990, Tetrahedron, 46, 65
S. Horito, K. Asano, K. Umemura, H. Hashimoto and J. Yoshimura, 1983, Carbohydrate Res., 121, 175
J. Yoshimura, K. Asano, K. Umemura, S. Horito and H. Hashimoto, 1983, Carbohydrate Res., 121, 187.
M. Trumtel, P. Tavecchia, A. Veyrieres and P. Sinay, 1990, Carbohydrate Res., 202, 257.
Y. Ito and T. Ogawa, 1987, Tetrahedron Lett., 28, 2723.
Y. Ito and T. Ogawa, 1987, Tetrahedron Lett., 28, 4701.
B.J. Fitzsimmons, Y. Leblanc and J. Rokach, 1987, J. Amer. Chem. Soc., 109, 285.
B.J. Fitzsimmons, Y. Leblanc, N. Chan and J. Rokach, 1988, J. Amer. Chem. Soc., 110, 5229.
D.A. Griffith and S.J. Danishefsky, 1990, J. Amer. Chem. Soc., 112, 5811.
D.A. Griffith and S.J. Danishefsky, 1991, J. Amer. Chem. Soc., 113, 5863.
F. Micheel and H. Wulff, 1956, Chem. Ber., 89, 1521
F. Micheel and E. Michaelis, 1958, Chem. Ber., 91, 188.
E. Kozlowska-Gramsz and G. Descotes, 1981, Tetrahedron Lett., 22, 563
E. Kozlowska-Gramsz and G. Descotes, 1982, Can. J. Chem., 60, 558.
R.L. Halcomb and S.J. Danishefsky, 1989, J. Amer. Chem. Soc., 111, 6661
R.G. Dushin and S.J. Danishefsky, 1992, J. Amer. Chem. Soc., 114, 3471.
K. Briner and A. Vasella, 1989, Helv. Chim. Acta, 72, 1371
K. Briner and A. Vasella, 1990, Helv. Chim. Acta, 73, 1764
A. Vasella, 1991, Pure and Appl. Chem., 63, 507.
J.M. Frechet and C. Schuerch, 1971, J. Amer. Chem. Soc., 93, 492
R.D. Guthrie, A.D. Jenkins and J. Stechlicek, 1971, J. Chem. Soc. (C), 2690
J.M. Frechet and C. Schuerch, 1972, Carbohydrate Res., 22, 399
U. Zehavi and A. Patchornik, 1973, J. Amer. Chem. Soc., 95, 5673
R. Eby and C. Schuerch, 1973, Carbohydrate Res., 27, 63
J.M. Frechet, 1981, Tetrahedron, 37, 663
U. Zehavi, 1988, Adv. Carbohydrate Chem. Biochem., 46, 179.
S.P. Douglas, D.M. Whitfield and J.J. Krepinsky, 1991, J. Amer. Chem. Soc., 113, 5095.
H. Kunz and B. Dombo, 1988, Angew. Chem. (Int. Edn.), 21, 111
H. Paulsen, G. Merz and U. Weichert, 1988, Angew. Chem. (Int. Edn.), 21, 1365
B. Luning, T. Norberg and J. Tejbrant, 1989; J. Chem. Soc. Chem. Comm., 1267.
S. David, C. Auge and C. Gautheron, 1991, Adv. Carbohydrate Chem. Biochem., 49, 175.
K.G.I. Nilsson, 1991, Appl. Biocat., 1, 117.
J.G. Buchanan, 1983, Progress in the Chemistry of Organic Natural Products, Vol IX, Eds. W. Herz, H. Grisebach and G.W. Kirby, Springer-Verlag, New York.
P. Lesimple, J.-M. Beau and P. Sinay, 1985, J. Chem. Soc. Chem. Comm., 894
J.-M. Beau and P. Sinay, 1985, Tetrahedron Lett., 26, 6185.
P. Deshong, G.A. Slough, V. Elango and G.L. Trainor, 1985, J. Amer. Chem. Soc., 107, 7788.
N. Chatani, T. Ikeda, T. Sano, N. Sonoda, H. Kurosawa, Y. Kawasaki and S. Murai, 1988, J. Org. Chem., 53, 3389.
U. Hacksen and G.D. Davies, Jr., 1983, J. Org. Chem., 48, 2870.
T.V. Rajanbabu, 1985, J. Org. Chem., 50, 3642.
R. Friesen and C.F. Sturino, 1990, J. Org. Chem., 55, 2572
R. Friesen and C.F. Sturino, 1990, J. Org. Chem., 55, 5808.
M.A. Tius, J. Gomez-Galeno, X. Gu and J.H. Zaidi, 1991, J. Amer. Chem. Soc., 113, 5775.
T. Matsumoto, M. Katsuki, H. Jona and K. Suzuki, 1991, J. Amer. Chem. Soc., 113, 6982.
G.H. Posner and S.R. Haines, 1985, Tetrahedron Lett., 26, 1823.
A.S. Kende, Y. Fujii and J.S. Mendoza, 1990, J. Amer. Chem. Soc., 112, 9645.
D. Zhai, W. Zhai and R.M. Williams, 1988, J. Amer. Chem. Soc., 110, 2501.
A.O. Stewart and R.M. Williams, 1985, J. Amer. Chem. Soc., 107, 4289.
P. Allevi, M. Anastasia, P. Giuffreda, A. Fiecchi and A. Scala, 1988, J. Chem. Soc. Chem. Comm., 57.
R. Bihovsky, C. Selick and I. Giusti, 1988, J. Org. Chem., 53, 4026.
V. Bellosta and S. Czernecki, 1989, J. Chem. Soc. Chem. Comm., 199.
G.E. Keck, E.J. Enholm, J.B. Yates and M.R. Wiley, 1985, Tetrahedron, 41, 4079.
G. Stork, H.S. Suh and G. Kim, 1991, J. Amer. Chem. Soc., 113, 7054.
See for example: R.E. Ireland, P.G.M. Wuts and B. Ernst, 1981, J. Amer. Chem. Soc., 103, 3205.
T.D. Aicher, K.R. Buszek, F.G. Fang, G.J. Forsyth, S.H. Jung, Y. Kishi and P.M. Scola, 1992, Tetrahedron Lett., 33, 1549.
M. Yamaguchi, A. Horiguchi, C. Ikeura and T. Minami, 1992, J. Chem. Soc. Chem. Comm., 434.
M. Yamaguchi, T. Okuma, A. Horiguchi, C. Ikeura and T. Minami, 1992, J. Org. Chem., 51, 1647.
D. Rolf and G.R. Gray, 1982, J. Amer. Chem. Soc., 104, 3539.
R. Tsang and B. Fraser-Reid, 1992, J. Org. Chem., 57, 1065.
J. Golik, J. Clardy, G. Dubay, G. Groenewold, H. Kawaguchi, M. Konishi, B. Krishnan, H. Ohkuma, K. Saitoh and T.W. Doyle, 1987, J. Amer. Chem. Soc., 109, 3461.
M.D. Lee, T.S. Dunne, M.M. Siegel, C.C. Chang, G.O. Morton and D.B. Borders, 1987, J. Amer. Chem. Soc., 109, 3464.
For a review see: K.C Nicolaou and W.M. Dai, 1991, Angew. Chem. (Int. Edn.), 30, 1387.
K.C. Nicolaou, R.D. Groneberg, T. Miyazaki, N.A. Stylianides, T.J. Schulze and W. Stahl, 1990, J. Amer. Chem. Soc., 112, 8193.
K.C Nicolaou and R.D. Groneberg, 1990, J. Amer. Chem. Soc., 112, 4085.
K.C. Nicolaou, R.D. Groneberg, N.A. Stylianides and T. Miyazki, 1990, J. Chem. Soc. Chem. Comm., 1275.
R.L. Halcomb, M.D. Wittman, S.H. Olsen, S.J. Danishefsky, J. Golik, H. Wong and D. Vyas, 1991, J. Amer. Chem. Soc., 113, 5080.
D. Yang, S.-H. Kim and D. Kahne, 1991, J. Amer. Chem. Soc., 113, 4715.
T.D. Inch, 1972, Adv. Carbohydrate Chem. Biochem., 27, 191.
K.J. Hale, Rodd’s Chemistry of Carbon Compounds, Vol I FG, 2nd Supplement, Ed. M. Sainsbury, Elsevier, Amsterdam, 1993, Chapter 23b.
H.U. Reissig, 1992, Angew. Chem. (Int. Edn.), 31, 288.
R. Selke and H. Pracejus, 1986, J. Mol. Catal., 37, 213.
I. Habus, Z. Raza and V. Sunjic, 1987, J. Mol. Catal., 42, 173.
M. Nogradi, 1987, Stereoselective Synthesis, VCH, Verlagsgesellschaft, Weinheim, 1987
H. Brunner, 1988, Synthesis, 645.
S. Saito, Y. Nakamura and Y. Morita, 1985, Chem. Pharm. Bull., 33, 5284.
M. Yamashita, M. Kobayashi, M. Sugiura, K. Tsunekawa, T. Oshikawa, S. Inokawa and H. Yamamoto, 1986, Bull. Chem. Soc. Jpn., 59, 175.
R. Selke, K. Haeupke and H.W. Krause, 1989, J. Mol. Catal., 56, 315.
H.C. Brown, W.S. Park and B.T. Cho, 1986, J. Org. Chem., 51, 1934, 3278, 3396
H.C. Brown, B.T. Cho and W.S. Park, 1988, J. Org. Chem., 53, 1231.
H.C. Brown, B.T. Cho and W.S. Park, 1987, J. Org. Chem., 52, 4020.
C.H. Heathcock, C.T. White, J.J. Morrison and D. VanDerveer, 1981, J. Org. Chem., 46, 1296.
R.O. Duthaler, P. Herold, W. Lottenbach, K. Oertle and M. Riediker, 1989, Angew. Chem. (Int. Edn.), 28, 495
R.O. Duthaler, A. Hafner and M. Riediker, 1990, Pure and Appl. Chem., 62, 631
K. Oertle, H. Beyeler, R.O. Duthaler, W. Lottenbach, M. Riediker and E. Steiner, 1990, Helv. Chim. Acta, 73, 353
R.O. Duthaler, P. Herold, S. Wyler-Helfer and M. Riedker, 1990, Helv. Chim. Acta, 73, 659.
G. Bold, R.O. Duthaler and M. Riediker, 1989, Angew. Chem. (Int. Edn.), 28, 497.
M. Riediker and R.O. Duthaler, 1989, Angew. Chem. (Int. Edn.), 28, 494.
D. Stanssens, D. De Keukeleire and M. Vandewalle, 1987, Tetrahedron Lett., 28, 4195
D. Stanssens, D. De Keukeleire and M. Vandewalle, 1990, Tetrahedron: Asymmetry, 1, 547.
R. Huber, A. Knierzinger, J.-P. Obrecht and A. Vasella, 1985, Helv. Chim. Acta, 68, 1730
B. Bernet, E. Krawczyk and A. Vasella, 1985, Helv. Chim. Acta, 68, 2299
R. Huber and A. Vasella, 1987, Helv. Chim. Acta, 70, 1461
R. Huber and A. Vasella, 1990, Tetrahedron, 46, 33.
S. Laschat and H. Kunz, 1992, Synthesis, 90.
J.M. Llera, I. Fernandez and F. Alcudia, 1991, Tetrahedron Lett., 32, 7299
D.D. Ridley and M.A. Smal, 1981, J. Chem. Soc. Chem. Comm., 505.
H. Kunz and W. Pfrengle, 1988, J. Amer. Chem. Soc., 110, 651
H. Kunz and W. Pfrengle, 1988, Tetrahedron, 44, 5487.
H. Kunz, W. Pfrengle and W. Sager, 1989, Tetrahedron Lett., 30, 4109.
H. Kunz, W. Pfrengle, K. Rueck and W. Sager, 1991, Synthesis, 1039.
H. Kunz and D. Schanzenbach, 1989, Angew. Chem. (Int. Edn.), 28, 1068.
S. Laschat and H. Kunz, 1990, Synlett, 51.
S. Laschat and H. Kunz, 1990, Synlett, 629.
T.K.M. Shing and P. Lloyd-Williams, 1987, J. Chem. Soc Chem. Comm., 423.
H. Kunz, B. Muller and D. Schanzenbach, 1987, Angew. Chem. (Int. Edn.), 26, 267.
W. Stahle and H. Kunz, 1991, Synlett, 260.
H. Felber, G. Kresze, H. Braun and A. Vasella, 1984, Tetrahedron Lett., 25, 5381
H. Felber, G. Kresze, R. Prewo and A. Vasella, 1986, Helv. Chim. Acta, 69, 1137
H. Braun, W. Burger, G. Kresze, F.P. Schmidtchen, J.L. Vaerman and H.G. Viehe, 1990, Tetrahedron: Asymmetry, 1, 403.
W. Pfrengle and H. Kunz, 1989, J. Org. Chem., 54, 4261.
R.C. Gupta, A.M.Z. Slawin, R.J. Stoodley and D.J. Williams, 1986, J. Chem. Soc. Chem. Comm., 668, 1116
R.C. Gupta, C.M. Raynor, R.J. Stoodley, A.M.Z. Slawin and D.J. Williams, 1988, J. Chem. Soc Perkin Trans. 1, 1113
R.C. Gupta, D.S. Larsen, R.J. Stoodley, A.M.Z. Slawin, and D.J. Williams, 1989, J. Chem. Soc. Perkin Trans. 1, 739
D.S. Larsen and R.J. Stoodley, 1989, J. Chem. Soc. Perkin Trans. 1, 1841.
B. Beagley, D.S. Larsen, R.G. Pritchard and R.J. Stoodley, 1989, J. Chem. Soc. Chem. Comm., 17.
C.W. Bird and A. Lewis, 1989, Tetrahedron Lett., 30, 6227.
A. Vasella, 1977, Helv. Chim. Acta, 60, 426, 1273
B. Bernet, E. Krawczyk and A. Vasella, 1985, Helv. Chim. Acta, 68, 2299.
A. Vasella and R. Voeffray, 1981, J. Chem. Soc. Chem. Comm., 97.
S. Mzengeza, C.M. Yang and R.A. Whitney, 1987, J. Amer. Chem. Soc., 109, 276
S. Mzengeza and R.A. Whitney, 1988, J. Org. Chem., 53, 4074.
B.C. Borer and D.W. Balogh, 1991, Tetrahedron Lett., 32, 1039.
A. Charette, B. Cote and J.-F. Marcoux, 1991, J. Amer. Chem. Soc., 113, 8166.
B. Fraser-Reid and R.C. Anderson, 1980, Fortschr. Chem. Org. Natust., Springer-Verlag, Wien
A. Vasella, Modern Synthetic Methods 1980, Ed. R. Scheffold Salle und Suerlander, Aurau, 1980
S. Hanessian, Total Synthesis of Natural Products: The Chiron Approach, Pergamon Press, Oxford, 1983
T.D. Inch, 1984, Tetrahedron, 40, 3161
K.J. Hale, Rodd’s Chemistry of Carbon Compounds, Vol I FG Supplements to 2nd Edn, Ed. M. Sainsbury, Elsevier, Amsterdam, 1993, Chapter 23c.
H.H. Pak, I.I. Canalda and B. Fraser-Reid, 1990, J. Org. Chem., 55, 3009.
N. Chida, M. Ohtsuka, K. Ogura and S. Ogawa, 1991, Bull. Chem. Soc. Jpn., 64, 2118.
N. Chida, M. Ohtsuka and S. Ogawa, 1991, Tetrahedron Lett., 32, 4525.
R. Grigg, V. Longanathan, V. Santhakumar, V. Sridharan and A. Teasdale, 1991, Tetrahedron Lett., 32, 687.
S. Mirza and A. Vasella, 1984, Helv. Chim. Acta, 67, 1562.
G.W.J. Fleet and T.K.M. Shing, 1983, J. Chem. Soc. Chem. Comm., 849
G.W.J. Fleet, T.K.M. Shing and S.M. Warr, 1984, J. Chem. Soc. Perkin Trans. 1, 905.
R.B. Gupta and R.W. Franck, 1989, J. Amer. Chem. Soc., 111, 7668.
A.B. Smith III, G.A. Sulikowski and K. Fujimoto, 1989, J. Amer. Chem. Soc., 111, 8039
A.B. Smith III, G.A. Sulikowski, M.M. Sulikowski and K. Fujimoto, 1992, J. Amer. Chem. Soc., 114, 2567.
G.W.J. Fleet, M.J. Gough, and P.W. Smith, 1984, Tetrahedron Lett., 25, 1853
B.P. Bhashyal, G.W.J. Fleet, M.J. Gough and P.W. Smith, 1987, Tetrahedron, 43, 3083.
K.C. Nicolaou, D.G. McGarry and P.K. Somers, 1990, J. Amer. Chem. Soc., 112, 3696
P.K. Somers, 1990, Ph.D. Thesis, University of Pennsylvania, Philadelphia, USA.
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1993 Springer Science+Business Media Dordrecht
About this chapter
Cite this chapter
Hale, K.J., Richardson, A.C. (1993). Carbohydrates. In: Thomson, R.H. (eds) The Chemistry of Natural Products. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-2144-6_1
Download citation
DOI: https://doi.org/10.1007/978-94-011-2144-6_1
Publisher Name: Springer, Dordrecht
Print ISBN: 978-94-010-4950-4
Online ISBN: 978-94-011-2144-6
eBook Packages: Springer Book Archive