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Volumn 38, Issue 34, 1997, Pages 5933-5936

A new approach to the pancratistatin C-ring from D-Glucose: Ferrier rearrangement, pseudoinversion and Pd-catalyzed cyclizations

Author keywords

[No Author keywords available]

Indexed keywords

7 DEOXYPANCRATISTATIN; ALKALOID; PANCRATISTATIN; UNCLASSIFIED DRUG;

EID: 0030786634     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01325-7     Document Type: Article
Times cited : (16)

References (49)
  • 1
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    • Amaryllidaceae alkaloids with antitumor activity
    • Hudlicky, T., Ed.; JAI Press, Inc.; Greenwich
    • Reviews: a) Polt, R. "Amaryllidaceae Alkaloids with Antitumor Activity" in Organic Synthesis: Theory and Applications, Hudlicky, T., Ed.; JAI Press, Inc.; Greenwich, 1996; Vol. 3, pp 109-148.
    • (1996) Organic Synthesis: Theory and Applications , vol.3 , pp. 109-148
    • Polt, R.1
  • 2
    • 77957033352 scopus 로고
    • Brossi, A.; Ed.; Academic Press: New York
    • b) Martin, S. F. In The Alkaloids; Brossi, A.; Ed.; Academic Press: New York, 1987; Vol. 30, pp 251-376.
    • (1987) The Alkaloids , vol.30 , pp. 251-376
    • Martin, S.F.1
  • 4
    • 0017032045 scopus 로고
    • a) Ohta, S.; Kimoto, S. Tetrahedron Lett. 1975, 2279; Chem. Pharm. Bull. 1976, 24, 2977.
    • (1976) Chem. Pharm. Bull. , vol.24 , pp. 2977
  • 7
    • 0019952166 scopus 로고
    • c) Paulsen, H.; Stubbe, M. Tetrahedron Lett. 1982, 23, 3171; Liebigs Ann. Chem. 1983, 535.
    • (1983) Liebigs Ann. Chem. , pp. 535
  • 36
    • 0342913279 scopus 로고    scopus 로고
    • Reference 2c describes a synthetic route to (+)-1 for which (+)-3 is an intermediate
    • Reference 2c describes a synthetic route to (+)-1 for which (+)-3 is an intermediate.
  • 37
    • 0342913277 scopus 로고    scopus 로고
    • This isomerization has precedent in the syntheses of 1, 3, and 4 described in references 2a, 2c, 3, and 5a
    • This isomerization has precedent in the syntheses of 1, 3, and 4 described in references 2a, 2c, 3, and 5a.
  • 39
    • 0027219906 scopus 로고
    • A recent publication describes an acyclic approach to an analogous D-carbohydrate L-carbohydrate conversion via "hidden C2 symmetry"; see: Furstner, A.; Baumgartner, J. Tetrahedron 1993, 49, 8541.
    • (1993) Tetrahedron , vol.49 , pp. 8541
    • Furstner, A.1    Baumgartner, J.2
  • 45
    • 0342478923 scopus 로고    scopus 로고
    • 4 in ethanol was complicated by base-induced enolization and subsequent elimination of BnOH
    • 4 in ethanol was complicated by base-induced enolization and subsequent elimination of BnOH.
  • 47
    • 0343784180 scopus 로고    scopus 로고
    • note
    • That only 21 and 22 were obtained demonstrated that 18b(α) and 18b(β), after silylation, each underwent highly stereospecific hydride reduction. Chromatographically separated 21 and 22 each furnished 20b upon Swern oxidation in parallel experiments.
  • 48
    • 0343784183 scopus 로고    scopus 로고
    • note
    • 1H NMR spectral data: For reductive cyclization, 23a:24a = 4:1 and 23b:24b = 5:1. For non-reductive cyclization, 24a:23a = 9:1 and 24b:23b = 12:1. Details are found in reference 7.
  • 49
    • 0342913271 scopus 로고    scopus 로고
    • note
    • 1H NMR coupling constant analysis. Prior to crystallographic analysis, we had misassigned this structure in an earlier communication (see reference 7).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.