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Volumn 47, Issue 19, 2008, Pages 3568-3572

Total synthesis and structural revision of callipeltoside C

Author keywords

Asymmetric synthesis; Callipeltoside C; Carbohydrates; Organocatalysis

Indexed keywords

CARBOHYDRATES; CHEMICAL REACTIONS; NETWORK PROTOCOLS; ORGANIC COMPOUNDS;

EID: 44049104472     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200800086     Document Type: Article
Times cited : (80)

References (42)
  • 17
  • 22
    • 0030025692 scopus 로고    scopus 로고
    • Stereochemistry has been previously established: K. Horita, T. Inoue, K. Tanaka, O. Yonemitsu, Tetrahedron 1996, 52, 531.
    • Stereochemistry has been previously established: K. Horita, T. Inoue, K. Tanaka, O. Yonemitsu, Tetrahedron 1996, 52, 531.
  • 23
    • 53549110947 scopus 로고    scopus 로고
    • D-proline catalysis: 12:1 anti/syn
    • With D-proline catalysis: 12:1 anti/syn, 1:2 Felkin/anti-Felkin.
    • 2 Felkin/anti-Felkin , vol.1
    • With1
  • 31
    • 0035932078 scopus 로고    scopus 로고
    • The side chain was synthesized according to the procedure of Evans: D. A. Evans, J. D. Burch, Org. Lett. 2001, 3, 503.
    • The side chain was synthesized according to the procedure of Evans: D. A. Evans, J. D. Burch, Org. Lett. 2001, 3, 503.
  • 32
    • 53549088466 scopus 로고    scopus 로고
    • The HWE coupling was less effective when performed after the macrocyclization step (84% vs. 54% yield).
    • The HWE coupling was less effective when performed after the macrocyclization step (84% vs. 54% yield).
  • 37
    • 53549132674 scopus 로고    scopus 로고
    • The macrolide 1 was formed as a 4:1 mixture of diastereomers at the anomeric position. Spectral data for each anomer was inconsistent with the characterization data for the natural isolate.
    • The macrolide 1 was formed as a 4:1 mixture of diastereomers at the anomeric position. Spectral data for each anomer was inconsistent with the characterization data for the natural isolate.
  • 38
    • 53549083385 scopus 로고    scopus 로고
    • We thank Professor L. Minale and co-workers for the Herculean taskof isolating and characterizing callipeltosides A-C. We thank Professor M. Valeria D'Auria for providing comparison spectra of natural 23 to D.W.C.M
    • We thank Professor L. Minale and co-workers for the Herculean taskof isolating and characterizing callipeltosides A-C. We thank Professor M. Valeria D'Auria for providing comparison spectra of natural 23 to D.W.C.M.
  • 39
    • 53549083094 scopus 로고    scopus 로고
    • At the present time we cannot state definitively the stereochemistry of the C1′ anomeric position of callipeltoside C. Based on the isolation studies for callipeltoside B, we tentatively suggest that it exists as the β-equatorial anomer as shown in Scheme 5
    • At the present time we cannot state definitively the stereochemistry of the C1′ anomeric position of callipeltoside C. Based on the isolation studies for callipeltoside B, we tentatively suggest that it exists as the β-equatorial anomer as shown in Scheme 5.
  • 40
    • 53549130851 scopus 로고    scopus 로고
    • We anticipate that the structure of callipeltoside B will likely be revised with respect to the enantiomer series of the pendent deoxyamino carbohydrate
    • We anticipate that the structure of callipeltoside B will likely be revised with respect to the enantiomer series of the pendent deoxyamino carbohydrate.
  • 41
    • 53549101509 scopus 로고    scopus 로고
    • The longest linear sequence is 18 steps and 12% overall yield from the Roche ester-derived aldehyde 6.
    • The longest linear sequence is 18 steps and 12% overall yield from the Roche ester-derived aldehyde 6.
  • 42
    • 34250684250 scopus 로고    scopus 로고
    • For a review on the organocatalytic synthesis of bioactive molecules
    • For a review on the organocatalytic synthesis of bioactive molecules: R. M. F. Figueirido, M. Christmann, Eur. J. Org. Chem. 2007, 2575.
    • (2007) Eur. J. Org. Chem , pp. 2575
    • Figueirido, R.M.F.1    Christmann, M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.