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Volumn 5, Issue 22, 2003, Pages 4037-4040

Total Synthesis of Zincophorin Methyl Ester

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; UNCLASSIFIED DRUG; ZINCOPHORIN METHYL ESTER;

EID: 0344083335     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035177n     Document Type: Article
Times cited : (31)

References (39)
  • 1
    • 0003910472 scopus 로고
    • Marcel Dekker: New York
    • Polyether Antibiotics; Westley, J. W., Ed.; Marcel Dekker: New York, 1982; Vols. 1 and 2.
    • (1982) Polyether Antibiotics , vol.1-2
    • Westley, J.W.1
  • 25
    • 0345584844 scopus 로고    scopus 로고
    • note
    • Structural assignment of the minor diastereomer 10 was supported by the fact that this compound was the only diastereomer generated (dr > 96/4) when the enantiomeric chiral allenylzinc (M)-7 derived from the mesylate (S)-8 was used as the nucleophile in the double-asymmetric condensation with aldehyde 6, which occurs in the matched manifold. The formation of 10 therefore arose from a partial racemization of the allenylmetal reagent during the condensation with aldehyde 6.
  • 26
    • 0344722615 scopus 로고    scopus 로고
    • note
    • 12 Addition of the chiral allenylzinc (P)-7 to aldehyde 6 according to a Felkin-Anh transition state (substrate control) could explain the formation of 11.
  • 30
  • 35
    • 0344722612 scopus 로고    scopus 로고
    • note
    • 16 in which the bulkier branched carbon chain, rather than the methyl group, should preferentially occupy the less congested equatorial position (Scheme 3).
  • 36
    • 0345584842 scopus 로고    scopus 로고
    • note
    • Carroll rearrangement of the related tertiary allylic β-ketoester 23, which affords ketone 24 as the major stereomer, has also been studied as a model. Ozonolysis of 24 led to the known (S)-keto aldehyde 25 (unpublished results). (Equation Presented)


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