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Volumn 2, Issue 2, 2000, Pages 223-226

Stereoselection in the Prins-pinacol synthesis of 2,2-disubstituted 4-acyltetrahydrofurans. Enantioselective synthesis of (-)-citreoviral

Author keywords

[No Author keywords available]

Indexed keywords

AUROVERTIN; CITREOVIRIDIN; FURAN DERIVATIVE; MYCOTOXIN; NEUROTOXIN;

EID: 0034719252     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991315q     Document Type: Article
Times cited : (58)

References (46)
  • 8
    • 0021225970 scopus 로고
    • The synthesis of asteltoxin by Schreiber and Satake is an early notable example: Schreiber, S. L.; Satake, K. J. Am. Chem. Soc. 1984, 106, 4186-4188.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 4186-4188
    • Schreiber, S.L.1    Satake, K.2
  • 25
    • 0001122697 scopus 로고
    • Trost, B. M., Heathcock, C. H., Eds.; Pergamon: Oxford
    • Colvin, E. W. In Comprehensive Organic Synthesis: Trost, B. M., Heathcock, C. H., Eds.; Pergamon: Oxford, 1992: Vol. 7, pp 641-651.
    • (1992) Comprehensive Organic Synthesis , vol.7 , pp. 641-651
    • Colvin, E.W.1
  • 27
    • 85037520595 scopus 로고    scopus 로고
    • note
    • 6c
  • 28
    • 85037521348 scopus 로고    scopus 로고
    • note
    • Stereochemical assignments for tetrahydrofuran products 13 and 14 were secured by nOe experiments. Details are provided in Supporting Information.
  • 33
    • 85037492126 scopus 로고    scopus 로고
    • note
    • 16 from condensation of 19 with the more accessible secondary trimethylsilyl ether group of 20 undergoes Prins cyclization faster than it is trapped by the proximal tertiary trimethylsilyl ether.
  • 35
    • 85037493312 scopus 로고    scopus 로고
    • note
    • A tetrahydrofuran product epimeric to 22 at C5 was not detected in this reaction or in the initial condensation of 19 and 20.
  • 36
    • 85037519811 scopus 로고    scopus 로고
    • note
    • The enantiopurity of 22 was confirmed by HPLC analysis using a Chiralcel OD column.
  • 40
    • 85037508407 scopus 로고    scopus 로고
    • note
    • At this point, the constitution of the tetrahydrofuran produced upon Prins-pinacol rearrangement was rigorously established by single-crystal X-ray analysis of the phenylcarbamate derivative.
  • 43
    • 85037514597 scopus 로고    scopus 로고
    • note
    • 5c have been reported for 1.
  • 44
    • 85037492194 scopus 로고    scopus 로고
    • note
    • 29
  • 45
    • 0030877492 scopus 로고    scopus 로고
    • For other reports documenting the high rate of the pinacol rearrangement step in Prins-pinacol rearrangements, see: (a) Minor, K. P.; Overman, L. E. Tetrahedron 1997, 53, 8927-8940.
    • (1997) Tetrahedron , vol.53 , pp. 8927-8940
    • Minor, K.P.1    Overman, L.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.