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Volumn , Issue 19, 2005, Pages 4082-4092

Stereoselective construction of a highly functionalized taxoid ABC-ring system: The C2-C9 oxa-bridge approach

Author keywords

Aldol reactions; Control elements; Samarium iodide; Taxoids; Transannular reactions

Indexed keywords


EID: 26444572947     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500347     Document Type: Article
Times cited : (11)

References (52)
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    • (1984) Asymmetric Synthesis , vol.3 , pp. 111-212
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  • 19
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    • The Zimmerman-Traxler transition state was first proposed for the Ivanov reaction: H. E. Zimmerman, M. D. Traxler, J. Am. Chem. Soc. 1957, 79, 1920-1923,
    • (1957) J. Am. Chem. Soc. , vol.79 , pp. 1920-1923
    • Zimmerman, H.E.1    Traxler, M.D.2
  • 20
    • 0002477225 scopus 로고
    • 1975: J. E. Dubois, P. Fellmann
    • while its first application to the aldol reaction was made by J. E. Dubois, in 1975: J. E. Dubois, P. Fellmann, Tetrahedron Lett. 1975, 16, 1225-1228. In the Zimmermann-Traxler transition state and Newman projection for the 2+3 aldol reaction, C9-H points towards the inside of the chair transition structure to minimize steric interactions: (Chemical Equation Presented)
    • (1975) Tetrahedron Lett. , vol.16 , pp. 1225-1228
    • Dubois, J.E.1
  • 29
    • 0003757056 scopus 로고
    • (Ed.: K. B. Wiberg), Part A, Academic Press, New York
    • R. Criegee, in: "Oxidation in Organic Chemistry" (Ed.: K. B. Wiberg), Part A, pp. 277-366. Academic Press, New York, 1965.
    • (1965) Oxidation in Organic Chemistry , pp. 277-366
    • Criegee, R.1
  • 41
    • 0001342880 scopus 로고    scopus 로고
    • d) W. A. Herrmann, F. E. Kühn, Acc. Chem. Res. 1997, 30, 169-180. The Sharpless group made substantial improvements to the original Hermann system by the addition of pyridine, which reduced the acidity of the reaction medium, allowing the synthesis of sensitive epoxides and enhanced catalyst activity:
    • (1997) Acc. Chem. Res. , vol.30 , pp. 169-180
    • Herrmann, W.A.1    Kühn, F.E.2
  • 47
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    • note
    • Hydrolytic removal of the ketal-protecting group was found to be sluggish, and normally reliable 1 N HCl/THF conditions failed due to competing breakdown of the acetonide protecting group.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.