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Volumn , Issue , 2005, Pages 575-628

Synthesis of carbohydrate containing complex natural compounds

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EID: 85056035631     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9781420027952     Document Type: Chapter
Times cited : (2)

References (94)
  • 5
    • 0035805264 scopus 로고    scopus 로고
    • Adventures in carbohydrate chemistry: New synthetic technologies, chemical synthesis, molecular design, and chemical biology
    • Nicolaou, K C, Mitchell, H J, Adventures in carbohydrate chemistry: new synthetic technologies, chemical synthesis, molecular design, and chemical biology, Angew. Chem. Int. Ed., 40, 1576-1624, 2001.
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 1576-1624
    • Nicolaou, K.C.1    Mitchell, H.J.2
  • 6
    • 0022636075 scopus 로고
    • New methods for the synthesis of glycosides and oligosaccharide-are there alternatives to the Koenigs-Knorr method?
    • Schmidt, R R, New methods for the synthesis of glycosides and oligosaccharide-are there alternatives to the Koenigs-Knorr method? Angew. Chem. Int. Ed., 25, 212-235, 1986.
    • (1986) Angew. Chem. Int. Ed , vol.25 , pp. 212-235
    • Schmidt, R.R.1
  • 7
    • 0001327985 scopus 로고
    • Recent advances in glycosylation reactions
    • Sinaÿ, P, Recent advances in glycosylation reactions, Pure Appl. Chem., 63, 519-528, 1991.
    • (1991) Pure Appl. Chem , vol.63 , pp. 519-528
    • Sinaÿ, P.1
  • 8
    • 5244279498 scopus 로고
    • Recent progress in O-glycosidation methods and its application to natural products synthesis
    • Toshima, K, Tatsuta, K, Recent progress in O-glycosidation methods and its application to natural products synthesis, Chem. Rev., 93, 1503-1531, 1993.
    • (1993) Chem. Rev , vol.93 , pp. 1503-1531
    • Toshima, K.1    Tatsuta, K.2
  • 9
    • 0030058793 scopus 로고    scopus 로고
    • Strategies in oligosaccharide synthesis
    • Boons, G J, Strategies in oligosaccharide synthesis, Tetrahedron, 52, 1095-1121, 1996.
    • (1996) Tetrahedron , vol.52 , pp. 1095-1121
    • Boons, G.J.1
  • 10
    • 0034698451 scopus 로고    scopus 로고
    • Recent developments in oligosaccharide synthesis
    • Davis, B G, Recent developments in oligosaccharide synthesis, J. Chem. Soc. Perkin. Trans. 1, 2137-2160, 2000.
    • (2000) J. Chem. Soc. Perkin. Trans. 1 , pp. 2137-2160
    • Davis, B.G.1
  • 18
    • 0026001317 scopus 로고
    • Application of efficient glycosylation of 2,6-anhydro-2-thio sugar to the total synthesis of erythromycin A
    • Toshima, K, Mukaiyama, S, Yoshida, T, Tamai, T, Tatsuta, K, Application of efficient glycosylation of 2,6-anhydro-2-thio sugar to the total synthesis of erythromycin A, Tetrahedron Lett., 32, 6155-6158, 1991.
    • (1991) Tetrahedron Lett , vol.32 , pp. 6155-6158
    • Toshima, K.1    Mukaiyama, S.2    Yoshida, T.3    Tamai, T.4    Tatsuta, K.5
  • 19
    • 0028936022 scopus 로고
    • Application of highly stereocontrolled glycosidations employing 2,6-anhydro-2-thio sugars to the syntheses of erythromycin A and olivomycin A trisaccharide
    • Toshima, K, Nozaki, Y, Mukaiyama, S, Tamai, T, Nakata, M, Tatsuta, K, Kinoshita, M, Application of highly stereocontrolled glycosidations employing 2,6-anhydro-2-thio sugars to the syntheses of erythromycin A and olivomycin A trisaccharide, J. Am. Chem. Soc., 117, 3717-3727, 1995.
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 3717-3727
    • Toshima, K.1    Nozaki, Y.2    Mukaiyama, S.3    Tamai, T.4    Nakata, M.5    Tatsuta, K.6    Kinoshita, M.7
  • 23
    • 0023812703 scopus 로고
    • First total synthesis of mycinamicin IV and VII. Successful application of new glycosidation reaction
    • Matsumoto, T, Maeta, H, Suzuki, K, Tsuchihashi, G, First total synthesis of mycinamicin IV and VII. Successful application of new glycosidation reaction, Tetrahedron Lett., 29, 3575-3578, 1988.
    • (1988) Tetrahedron Lett , vol.29 , pp. 3575-3578
    • Matsumoto, T.1    Maeta, H.2    Suzuki, K.3    Tsuchihashi, G.4
  • 33
    • 0021804358 scopus 로고
    • Carbohydrate-based synthesis of the goldinonolactone and the tetrahydrofuran fragment of aurodox and efrotomycin
    • Dolle, R E, Nicolaou, K C, Carbohydrate-based synthesis of the goldinonolactone and the tetrahydrofuran fragment of aurodox and efrotomycin, J. Chem. Soc. Chem. Commun., 1016-1985, 1985.
    • (1985) J. Chem. Soc. Chem. Commun , pp. 1016-1985
    • Dolle, R.E.1    Nicolaou, K.C.2
  • 34
    • 0021998102 scopus 로고
    • Total synthesis of elfamycins: Aurodox and efrotomycin. 1. Strategy and construction of key intermediates
    • Dolle, R E, Nicolaou, K C, Total synthesis of elfamycins: aurodox and efrotomycin. 1. Strategy and construction of key intermediates, J. Am. Chem. Soc., 107, 1691-1694, 1985.
    • (1985) J. Am. Chem. Soc , vol.107 , pp. 1691-1694
    • Dolle, R.E.1    Nicolaou, K.C.2
  • 35
    • 0021919844 scopus 로고
    • Total synthesis of Elfamycins: Aurodox and efrotomycin. 2. Coupling of key intermediates and completion of the synthesis
    • Dolle, R E, Nicolaou, K C, Total synthesis of Elfamycins: aurodox and efrotomycin. 2. Coupling of key intermediates and completion of the synthesis, J. Am. Chem. Soc., 107, 1695-1698, 1985.
    • (1985) J. Am. Chem. Soc , vol.107 , pp. 1695-1698
    • Dolle, R.E.1    Nicolaou, K.C.2
  • 36
    • 0023158140 scopus 로고
    • Stereocontrolled construction of key building blocks for the total synthesis of amphoteronolide B and amphotericin B
    • Nicolaou, K C, Daines, R A, Uenishi, J, Li, W S, Papahatjis, D P, Chakraborty, T K, Stereocontrolled construction of key building blocks for the total synthesis of amphoteronolide B and amphotericin B, J. Am. Chem. Soc., 109, 2205-2208, 1987.
    • (1987) J. Am. Chem. Soc , vol.109 , pp. 2205-2208
    • Nicolaou, K.C.1    Daines, R.A.2    Uenishi, J.3    Li, W.S.4    Papahatjis, D.P.5    Chakraborty, T.K.6
  • 39
    • 0023740262 scopus 로고
    • Total synthesis of amphoteronolide B and amphotericin B. 1. Strategy and stereocontrolled construction of key building blocks
    • Nicolaou, C, Daines, R A, Uenishi, J, Li, W S, Papahatjis, D P, Chakraborty, T K, Total synthesis of amphoteronolide B and amphotericin B. 1. Strategy and stereocontrolled construction of key building blocks, J. Am. Chem. Soc., 110, 4672-4685, 1988.
    • (1988) J. Am. Chem. Soc , vol.110 , pp. 4672-4685
    • Nicolaou, C.1    Daines, R.A.2    Uenishi, J.3    Li, W.S.4    Papahatjis, D.P.5    Chakraborty, T.K.6
  • 40
    • 0023785976 scopus 로고
    • Total synthesis of amphoteronolide B and amphotericin B. 2. Total synthesis of amphoteronolide B
    • Nicolaou, K C, Daines, R A, Chakraborty, T K, Ogawa, Y, Total synthesis of amphoteronolide B and amphotericin B. 2. Total synthesis of amphoteronolide B, J. Am. Chem. Soc., 110, 4685-4696, 1988.
    • (1988) J. Am. Chem. Soc , vol.110 , pp. 4685-4696
    • Nicolaou, K.C.1    Daines, R.A.2    Chakraborty, T.K.3    Ogawa, Y.4
  • 42
    • 0022470772 scopus 로고
    • Total synthesis of elaiophylin (azalomycin B)
    • Toshima, K, Tatsuta, K, Kinoshita, M, Total synthesis of elaiophylin (azalomycin B), Tetrahedron Lett., 27, 4741-4744, 1986.
    • (1986) Tetrahedron Lett , vol.27 , pp. 4741-4744
    • Toshima, K.1    Tatsuta, K.2    Kinoshita, M.3
  • 52
    • 0029038220 scopus 로고
    • Studies related to the carbohydrate sectors of esperamicin and calicheamicin: Definition of the stability limits of the esperamicin domain and fashioning of a glycosyl donor from the calicheamicin domain
    • Halcomb, R L, Boyer, S H, Wittman, M D, Olson, S H, Denhart, D J, Liu, K K C, Danishefsky, S J, Studies related to the carbohydrate sectors of esperamicin and calicheamicin: definition of the stability limits of the esperamicin domain and fashioning of a glycosyl donor from the calicheamicin domain, J. Am. Chem. Soc., 117, 5720-5749, 1995.
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 5720-5749
    • Halcomb, R.L.1    Boyer, S.H.2    Wittman, M.D.3    Olson, S.H.4    Denhart, D.J.5    Liu, K.K.C.6    Danishefsky, S.J.7
  • 59
    • 0027098097 scopus 로고
    • An improved synthesis of naphthoate precursors to olivine
    • Roush, W R, Murphy, M, An improved synthesis of naphthoate precursors to olivine, J. Org. Chem., 57, 6622-6629, 1992.
    • (1992) J. Org. Chem , vol.57 , pp. 6622-6629
    • Roush, W.R.1    Murphy, M.2
  • 60
    • 0028912353 scopus 로고
    • Studies on the synthesis of aureolic acid antibiotics: Highly stereoselective synthesis of aryl 2-deoxy-b-glycosides via the Mitsunobu reaction and synthesis of the olivomycin A-B disaccharide
    • Roush, W R, Lin, X F, Studies on the synthesis of aureolic acid antibiotics: Highly stereoselective synthesis of aryl 2-deoxy-b-glycosides via the Mitsunobu reaction and synthesis of the olivomycin A-B disaccharide, J. Am. Chem. Soc., 117, 2236-2250, 1995.
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 2236-2250
    • Roush, W.R.1    Lin, X.F.2
  • 64
    • 0033571255 scopus 로고    scopus 로고
    • Total synthesis of everninomicin 13,384-1-part 3: Synthesis of the DE fragment and completion of the total synthesis
    • Nicolaou, K C, Mitchell, H J, Rodríguez, R M, Fylaktakidou, K C, Suzuki, H, Total synthesis of everninomicin 13,384-1-part 3: synthesis of the DE fragment and completion of the total synthesis, Angew. Chem. Int. Ed., 38, 3345-3350, 1999.
    • (1999) Angew. Chem. Int. Ed , vol.38 , pp. 3345-3350
    • Nicolaou, K.C.1    Mitchell, H.J.2    Rodríguez, R.M.3    Fylaktakidou, K.C.4    Suzuki, H.5
  • 65
    • 0001819191 scopus 로고
    • Relative configuration of a marine toxin polycavernoside A
    • Fujiwara, K, Amano, S, Murai, A, Relative configuration of a marine toxin polycavernoside A, Chem Lett, 855-856, 1995.
    • (1995) Chem Lett , pp. 855-856
    • Fujiwara, K.1    Amano, S.2    Murai, A.3
  • 66
    • 0032556235 scopus 로고
    • Total synthesis of and absolute configuration of polycavernoside A
    • Fujiwara, K, Murai, A, Yotsu-Yamashita, M, Yasumoto, T, Total synthesis of and absolute configuration of polycavernoside A, J. Am. Chem. Soc., 120, 10770-10771, 1988.
    • (1988) J. Am. Chem. Soc , vol.120 , pp. 10770-10771
    • Fujiwara, K.1    Murai, A.2    Yotsu-Yamashita, M.3    Yasumoto, T.4
  • 67
    • 0029062094 scopus 로고
    • Studies directed toward the total synthesis of polycavernoside A, Enantioselective synthesis of the disaccharide component
    • Johnston, J N, Paquette, L A, Studies directed toward the total synthesis of polycavernoside A, Enantioselective synthesis of the disaccharide component. Tetrahedron Lett., 36, 4341-4344, 1995.
    • (1995) Tetrahedron Lett , vol.36 , pp. 4341-4344
    • Johnston, J.N.1    Paquette, L.A.2
  • 68
    • 0033549091 scopus 로고    scopus 로고
    • A convergent total synthesis of the macrolactone disaccharide toxin (2)-polycavernoside A
    • Paquette, L A, Barriault, L, Pissarnitski, D, A convergent total synthesis of the macrolactone disaccharide toxin (2)-polycavernoside A, J. Am. Chem. Soc., 121, 4542-4543, 1999.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 4542-4543
    • Paquette, L.A.1    Barriault, L.2    Pissarnitski, D.3
  • 77
    • 0033577010 scopus 로고    scopus 로고
    • Synthesis of vancomycin from the aglycon
    • Thompson, C, Ge, M, Kahne, D, Synthesis of vancomycin from the aglycon, J. Am. Chem. Soc., 121, 1237-1244, 1999.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 1237-1244
    • Thompson, C.1    Ge, M.2    Kahne, D.3
  • 79
    • 0035887506 scopus 로고    scopus 로고
    • Total synthesis of apoptolidin: Part 2. Coupling of key building blocks and completion of the synthesis
    • Nicolaou, K C, Li, Y, Fylaktakidou, K C, Mitchell, H J, Sugita, K, Total synthesis of apoptolidin: part 2. Coupling of key building blocks and completion of the synthesis, Angew. Chem. Int. Ed., 40, 3854-3857, 2001.
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 3854-3857
    • Nicolaou, K.C.1    Li, Y.2    Fylaktakidou, K.C.3    Mitchell, H.J.4    Sugita, K.5
  • 83
    • 0025042187 scopus 로고
    • Enantioselective total synthesis of medermycin (lactoquinomycin)
    • Tatsuta, K, Ozaki, H, Yamaguchi, M, Tanaka, M, Okui, T, Enantioselective total synthesis of medermycin (lactoquinomycin), Tetrahedron Lett., 31, 5495-5498, 1990.
    • (1990) Tetrahedron Lett , vol.31 , pp. 5495-5498
    • Tatsuta, K.1    Ozaki, H.2    Yamaguchi, M.3    Tanaka, M.4    Okui, T.5
  • 85
    • 0026588424 scopus 로고
    • Total synthesis of (2)-urdamycinone B through polyketide condensation
    • Yamaguchi, M, Okumura, T, Horiguchi, A, Ikeura, C, Minami, T, Total synthesis of (2)-urdamycinone B through polyketide condensation, J. Org. Chem., 57, 1647-1649, 1992.
    • (1992) J. Org. Chem , vol.57 , pp. 1647-1649
    • Yamaguchi, M.1    Okumura, T.2    Horiguchi, A.3    Ikeura, C.4    Minami, T.5
  • 86
    • 33751386487 scopus 로고
    • Preparation of 2-deoxy-b-C-arylglycosides and C-arylglycosides from carbohydrate lactones
    • Boyd, V A, Drake, B E, Sulikowski, G A, Preparation of 2-deoxy-b-C-arylglycosides and C-arylglycosides from carbohydrate lactones, J. Org. Chem., 58, 3191-3193, 1993.
    • (1993) J. Org. Chem , vol.58 , pp. 3191-3193
    • Boyd, V.A.1    Drake, B.E.2    Sulikowski, G.A.3
  • 87
    • 0029120877 scopus 로고
    • Total synthesis of the angucycline antibiotics urdamycinone B and 104-2 via a common synthetic intermediate
    • Boyd, V A, Sulikowski, G A, Total synthesis of the angucycline antibiotics urdamycinone B and 104-2 via a common synthetic intermediate, J. Am. Chem. Soc., 117, 8472-8473, 1995.
    • (1995) J. Am. Chem. Soc , vol.117 , pp. 8472-8473
    • Boyd, V.A.1    Sulikowski, G.A.2
  • 88
    • 0030056863 scopus 로고    scopus 로고
    • Total synthesis of urdamycinone B via C-glycosidation of an unprotected sugar and Diels-Alder reaction of C-glycosyl juglone
    • Matsuo, G, Miki, Y, Nakata, M, Matsumura, S, Toshima, K, Total synthesis of urdamycinone B via C-glycosidation of an unprotected sugar and Diels-Alder reaction of C-glycosyl juglone, Chem. Commun., 225-226, 1996.
    • (1996) Chem. Commun , pp. 225-226
    • Matsuo, G.1    Miki, Y.2    Nakata, M.3    Matsumura, S.4    Toshima, K.5
  • 89
    • 0029761762 scopus 로고    scopus 로고
    • Two-step synthesis of C-glycosyl juglones from unprotected sugars: A novel approach to angucycline antibiotics
    • Matsuo, G, Matsumura, S, Toshima, K, Two-step synthesis of C-glycosyl juglones from unprotected sugars: a novel approach to angucycline antibiotics, Chem. Commun., 2173-2174, 1996.
    • (1996) Chem. Commun , pp. 2173-2174
    • Matsuo, G.1    Matsumura, S.2    Toshima, K.3
  • 90
    • 0033578798 scopus 로고    scopus 로고
    • Total synthesis of C-glycosylangucycline, urdamycinone B, using an unprotected sugar
    • Matsuo, G, Miki, Y, Nakata, M, Matsumura, S, Toshima, K, Total synthesis of C-glycosylangucycline, urdamycinone B, using an unprotected sugar, J. Org. Chem., 64, 7101-7106, 1999.
    • (1999) J. Org. Chem , vol.64 , pp. 7101-7106
    • Matsuo, G.1    Miki, Y.2    Nakata, M.3    Matsumura, S.4    Toshima, K.5
  • 91
    • 0026590352 scopus 로고
    • Total synthesis and absolute stereochemical assignment of gilvocarcin M
    • Matsumoto, T, Hosoya, T, Suzuki, K, Total synthesis and absolute stereochemical assignment of gilvocarcin M, J. Am. Chem. Soc., 114, 3568-3570, 1992.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 3568-3570
    • Matsumoto, T.1    Hosoya, T.2    Suzuki, K.3
  • 93
    • 0033616086 scopus 로고    scopus 로고
    • First synthesis of a bidesmosidic triterpene saponin by a highly efficient procedure
    • Yu, B, Xie, J, Deng, S, Hui, Y, First synthesis of a bidesmosidic triterpene saponin by a highly efficient procedure, J. Am. Chem. Soc., 121, 12196-12197, 1999.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 12196-12197
    • Yu, B.1    Xie, J.2    Deng, S.3    Hui, Y.4
  • 94
    • 0035476321 scopus 로고    scopus 로고
    • Convergent synthesis of digitoxin: Stereoselective synthesis and glycosylation of the digoxin trisaccharide glycal
    • McDonald, F E, Reddy, K S, Convergent synthesis of digitoxin: stereoselective synthesis and glycosylation of the digoxin trisaccharide glycal, Angew. Chem. Int. Ed., 40, 3653-3655, 2001.
    • (2001) Angew. Chem. Int. Ed , vol.40 , pp. 3653-3655
    • McDonald, F.E.1    Reddy, K.S.2


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