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Volumn 55, Issue 7, 1999, Pages 1905-1914

trans-C-glycosides from 8-oxabicyclo[3.2.1]oct-6-en-3-one - Synthesis of the C3-C13 segment of the phorboxazoles A and B

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; MACROLIDE; PHORBOXAZOLE A; PHORBOXAZOLE B; UNCLASSIFIED DRUG;

EID: 0033548011     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01196-X     Document Type: Article
Times cited : (60)

References (38)
  • 4
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    • Taxol ®
    • Taxol ®: Nicolaou, K. C.; Dai, W. M.; Guy, R. K. Angew. Chem. 1994, 106, 38; Angew. Chem. Int. Ed. Engl. 1994. 33, 15; see also Nicolaou. K. C. and Sorensen, E. J. Classics in Total Synthesis. VCH, Weinheim, 1996.
    • (1994) Angew. Chem. , vol.106 , pp. 38
    • Nicolaou, K.C.1    Dai, W.M.2    Guy, R.K.3
  • 5
    • 0003185761 scopus 로고
    • Taxol ®: Nicolaou, K. C.; Dai, W. M.; Guy, R. K. Angew. Chem. 1994, 106, 38; Angew. Chem. Int. Ed. Engl. 1994. 33, 15; see also Nicolaou. K. C. and Sorensen, E. J. Classics in Total Synthesis. VCH, Weinheim, 1996.
    • (1994) Angew. Chem. Int. Ed. Engl. , vol.33 , pp. 15
  • 6
    • 0004220870 scopus 로고    scopus 로고
    • VCH, Weinheim
    • Taxol ®: Nicolaou, K. C.; Dai, W. M.; Guy, R. K. Angew. Chem. 1994, 106, 38; Angew. Chem. Int. Ed. Engl. 1994. 33, 15; see also Nicolaou. K. C. and Sorensen, E. J. Classics in Total Synthesis. VCH, Weinheim, 1996.
    • (1996) Classics in Total Synthesis
    • Nicolaou, K.C.1    Sorensen, E.J.2
  • 7
    • 0000149648 scopus 로고    scopus 로고
    • An excellent review of the epothilones is given in
    • An excellent review of the epothilones is given in: Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem. 1998, 110, 2120; Angew. Chem. Int. Ed. Engl. 1998, 37, 2014.
    • (1998) Angew. Chem. , vol.110 , pp. 2120
    • Nicolaou, K.C.1    Roschangar, F.2    Vourloumis, D.3
  • 8
    • 0032541259 scopus 로고    scopus 로고
    • An excellent review of the epothilones is given in: Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem. 1998, 110, 2120; Angew. Chem. Int. Ed. Engl. 1998, 37, 2014.
    • (1998) Angew. Chem. Int. Ed. Engl. , vol.37 , pp. 2014
  • 28
    • 0030796701 scopus 로고    scopus 로고
    • and literature cited therein
    • c) Kishi, Y.; Minehan, T. G. Tetrahedron Lett. 1997, 38, 6815 and literature cited therein.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 6815
    • Kishi, Y.1    Minehan, T.G.2
  • 29
    • 0013621844 scopus 로고    scopus 로고
    • When dimethylsulfide was used, the reduction was rather slow
    • When dimethylsulfide was used, the reduction was rather slow.
  • 33
    • 0009924476 scopus 로고
    • Stereocenter C7 of aldehydes 12 and 14 is stereogenic; for identical side arms this center becomes chirotopic; local chirality is discussed in: (formula presented)
    • b) Stereocenter C7 of aldehydes 12 and 14 is stereogenic; for identical side arms this center becomes chirotopic; local chirality is discussed in: Mislow, K.; Siegel, J. J. Am. Chem. Soc. 1984, 106, 3319. (formula presented)
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 3319
    • Mislow, K.1    Siegel, J.2
  • 37
    • 0013620516 scopus 로고    scopus 로고
    • The use of TBS-chloride for O-silylation was totally ineffective; we explain this fact with the intramolecular hydrogen bonding of the alcohol group (cf. Figure 2)
    • The use of TBS-chloride for O-silylation was totally ineffective; we explain this fact with the intramolecular hydrogen bonding of the alcohol group (cf. Figure 2).


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