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Volumn 3, Issue 2, 2006, Pages 140-142

Stereoselective total synthesis of (+)-sedamine

Author keywords

(+) sedamine; ADH; RCM; Regioselective epoxide opening; Vinylmetallic reagent

Indexed keywords


EID: 34247096966     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806775224297     Document Type: Article
Times cited : (6)

References (23)
  • 3
    • 34247151008 scopus 로고    scopus 로고
    • Meth-Cohn, O.; Yu, C.-Y.; Lestage, P.; Leburn, M.-C.; Cagniard, D.-H.; Renard, P. Eur. Pat. 1050531, 2000.
    • Meth-Cohn, O.; Yu, C.-Y.; Lestage, P.; Leburn, M.-C.; Cagniard, D.-H.; Renard, P. Eur. Pat. 1050531, 2000.
  • 5
    • 0037157808 scopus 로고    scopus 로고
    • For a review see: a
    • For a review see: (a) Bates, R. W.; Sa-Ei, K. Tetrahedron 2002, 58, 5957;
    • (2002) Tetrahedron , vol.58 , pp. 5957
    • Bates, R.W.1    Sa-Ei, K.2
  • 13
    • 34247113613 scopus 로고    scopus 로고
    • See: Reference [5] (c).
    • See: Reference [5] (c).
  • 14
    • 34247145814 scopus 로고    scopus 로고
    • Chiral styrene oxide 6 was prepared in 88% overall yield in three steps with 98% ee, following the sequence. A figure is presented.
    • Chiral styrene oxide 6 was prepared in 88% overall yield in three steps with 98% ee, following the sequence. A figure is presented.
  • 16
    • 34247163036 scopus 로고    scopus 로고
    • The enantiomeric excess (ee) was measured by HPLC analysis carried using a Waters 510 HPLC system. Chiracel OD packed in a ss column of 4.6 mm i.d. X 250 m was used. Isocratic elution was applied with a mobile phase consisting of n-Hexane 90% and isopropanol 10% at a flow rate of 0.8 mL/ min and a pressure of 125 psi. UV detection at 243 nm was used. Retention time 5.5 and 7.8 min.
    • The enantiomeric excess (ee) was measured by HPLC analysis carried using a Waters 510 HPLC system. Chiracel OD packed in a ss column of 4.6 mm i.d. X 250 m was used. Isocratic elution was applied with a mobile phase consisting of n-Hexane 90% and isopropanol 10% at a flow rate of 0.8 mL/ min and a pressure of 125 psi. UV detection at 243 nm was used. Retention time 5.5 and 7.8 min.
  • 19
    • 34247175223 scopus 로고    scopus 로고
    • 1H NMR (300 MHz) of the crude product mixture. A figure is presented.
    • 1H NMR (300 MHz) of the crude product mixture. A figure is presented.
  • 21
    • 34247151478 scopus 로고    scopus 로고
    • 4-Cobalt (II) chloride in water although resulted in clean conversion of the starting material, during the work-up complete decomposition occurred.
    • 4-Cobalt (II) chloride in water although resulted in clean conversion of the starting material, during the work-up complete decomposition occurred.
  • 22
    • 0344006321 scopus 로고    scopus 로고
    • For recent reviews on ring closing metathesis see: a
    • For recent reviews on ring closing metathesis see: (a) Füerstner, A. Angew. Chem. Int. Ed. 2000, 39, 3013;
    • (2000) Angew. Chem. Int. Ed , vol.39 , pp. 3013
    • Füerstner, A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.