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Volumn 12, Issue 1, 2005, Pages 76-89

Concise approach to the "higher sugar" core of the nucleoside antibiotic hikizimycin

Author keywords

Carbohydrates; Chromium; Dihydroxylation; Natural products; Ruthenium

Indexed keywords

ACYCLIC SUBSTRATE; DIASTEREOMER; DIHYDROXYLATION; NATURAL PRODUCTS;

EID: 29344454053     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200500791     Document Type: Article
Times cited : (50)

References (117)
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    • Glycomimetics: Modern Synthetic Methodologies (Ed.: R. Roy), American Chemical Society, Washington
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    • While the directing influence of allylic oxygen substituents has been studied in detail (cf. ref. [21]), the effect of allylic phthalimides is not nearly as well understood; for a pertinent example showing that osmylations of allyic phthalimides also obey Kishi's rule (although the directing effect is lower than that of allylic alcohols) see: J. Mulzer, C. Brand, Tetrahedron 1986, 42, 5961-5968.
    • (1986) Tetrahedron , vol.42 , pp. 5961-5968
    • Mulzer, J.1    Brand, C.2
  • 62
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    • Reviews: a) A. Fürstner, Chem. Rev. 1999, 99, 991-1045;
    • (1999) Chem. Rev. , vol.99 , pp. 991-1045
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    • b) K. Takai, Org. React. 2004, 64, 253-612;
    • (2004) Org. React. , vol.64 , pp. 253-612
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    • g) C. Chen, Synlett 1998, 1311-1312;
    • (1998) Synlett , pp. 1311-1312
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    • note
    • During the course of the reaction, the excess alkynyl iodide 12 was reduced to alkyne 11 which could be recovered by flash chromatography.
  • 94
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    • see ref. [32b]
    • a) see ref. [32b];
  • 103
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    • note
    • The inversed order of reactions, that is, Mitsunobu reaction at the stage of the propargyl alcohol 18 followed by semi-reduction, was much less effective because the Lindlar step did not proceed well likely due to the increased steric hindrance exerted by the adjacent phthalimide residue.
  • 105
    • 29344441510 scopus 로고    scopus 로고
    • note
    • 4-catalyzed process, we confidently ascribe the same stereochemistry to the resulting osmate esters as that observed in 31α and pyranose 32 derived thereof.
  • 106
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    • 3C from the trichloroacetamido group in a "haloform"-type process rather than the expected diol 27b. For a related transformation see: S. H. Kang, H. Choi, J. S. Kim, J.-H. Youn, Chem. Commun. 2000, 227-228.
    • (2000) Chem. Commun. , pp. 227-228
    • Kang, S.H.1    Choi, H.2    Kim, J.S.3    Youn, J.-H.4
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    • note
    • H-1,H-2 = 7.3 Hz is somewhat ambiguous and could be compatible with either an α- or a β-configuration at the anomeric center; note, however, that the final thioglycoside 33 derived from 32 is α-configured, see Scheme 10.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.