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Volumn 45, Issue 2, 2004, Pages 421-423

A concise and stereoselective synthesis of (+)- and (-)-deoxoprosophylline

Author keywords

Claisen rearrangement; Deoxoprosophylline; Piperidine alkaloids; Sharpless asymmetric dihydroxylation

Indexed keywords

ALKALOID DERIVATIVE; DEOXOPROSOPHYLLINE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0346366640     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.142     Document Type: Article
Times cited : (41)

References (25)
  • 1
    • 77957037489 scopus 로고    scopus 로고
    • Pyridine and Piperidine Alkaloids: An Update
    • Pelletier S.W. Oxford: Pergamon
    • Schneider M.J. Pyridine and Piperidine Alkaloids: An Update. Pelletier S.W. Alkaloids: Chemical and Biological Perspectives. Vol. 10:1996;155-299 Pergamon, Oxford.
    • (1996) Alkaloids: Chemical and Biological Perspectives , vol.10 , pp. 155-299
    • Schneider, M.J.1
  • 17
    • 33750247077 scopus 로고    scopus 로고
    • For a review on asymmetric dihydroxylation, see: (a) Becker H., Sharpless K.B. Angew. Chem., Int. Ed. Engl. 35:1996;448-481 (b) Torri S., Liu P., Bhuvaneswari N., Amatore C., Jutand A. J. Org. Chem. 61:1996;3055-3060 (c) . For a review on asymmetric dihydroxylation, see: Kolb H.C., Van Niewenhze M.S., Sharpless K.B. Chem. Rev. 94:1994;2483-2547 (d) The ee of the compound 8 was determined to be 93% by Chiral HPLC analysis (Chiralcel OD, 80:20 hexane/i-PrOH, 1 mL/min, 254 nm).
    • (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 448-481
    • Becker, H.1    Sharpless, K.B.2
  • 18
    • 33750247077 scopus 로고    scopus 로고
    • For a review on asymmetric dihydroxylation, see: (a) Becker H., Sharpless K.B. Angew. Chem., Int. Ed. Engl. 35:1996;448-481 (b) Torri S., Liu P., Bhuvaneswari N., Amatore C., Jutand A. J. Org. Chem. 61:1996;3055-3060 (c) . For a review on asymmetric dihydroxylation, see: Kolb H.C., Van Niewenhze M.S., Sharpless K.B. Chem. Rev. 94:1994;2483-2547 (d) The ee of the compound 8 was determined to be 93% by Chiral HPLC analysis (Chiralcel OD, 80:20 hexane/i-PrOH, 1 mL/min, 254 nm).
    • (1996) J. Org. Chem. , vol.61 , pp. 3055-3060
    • Torri, S.1    Liu, P.2    Bhuvaneswari, N.3    Amatore, C.4    Jutand, A.5
  • 19
    • 4444276636 scopus 로고
    • For a review on asymmetric dihydroxylation, see: (a) Becker H., Sharpless K.B. Angew. Chem., Int. Ed. Engl. 35:1996;448-481 (b) Torri S., Liu P., Bhuvaneswari N., Amatore C., Jutand A. J. Org. Chem. 61:1996;3055-3060 (c) . For a review on asymmetric dihydroxylation, see: Kolb H.C., Van Niewenhze M.S., Sharpless K.B. Chem. Rev. 94:1994;2483-2547 (d) The ee of the compound 8 was determined to be 93% by Chiral HPLC analysis (Chiralcel OD, 80:20 hexane/i-PrOH, 1 mL/min, 254 nm).
    • (1994) Chem. Rev. , vol.94 , pp. 2483-2547
    • Kolb, H.C.1    Van Niewenhze, M.S.2    Sharpless, K.B.3
  • 25
    • 85030919340 scopus 로고    scopus 로고
    • 13CNMR(50MHz)δ:14.18,22.75,26.27,29.37,29.7,29.8,30.83,31.97, 33.77,36.35,56.23,63.4,63.88,69.8ppm
    • 13C NMR (50 MHz) δ : 14.18, 22.75, 26.27, 29.37, 29.7, 29.8, 30.83, 31.97, 33.77, 36.35, 56.23, 63.4, 63.88, 69.8 ppm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.