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Volumn 8, Issue 14, 2006, Pages 2993-2996

Total synthesis of cryptophycin analogues via a scaffold approach

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ANTIMITOTIC AGENT; CRYPTOPHYCIN; CYCLOPEPTIDE; DEPSIPEPTIDE; VINYL DERIVATIVE;

EID: 33746641274     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0609356     Document Type: Article
Times cited : (39)

References (52)
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    • (b) Hong, J.; Zhang, L. In Frontiers of Biotechnology and Pharmaceuticals; Zhao, K., Reiner J., Chen, S.-H., Eds.; Science Press New York Ltd.: New York, 2002; p 193.
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    • Zhao, K., Reiner, J., Chen, S.-H., Eds.; Science Press New York Ltd.: New York
    • (c) Li, T.; Shih, C. In Frontiers of Biotechnology and Pharmaceuticals; Zhao, K., Reiner, J., Chen, S.-H., Eds.; Science Press New York Ltd.: New York, 2002; p 172.
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    • (c) Avila, J. FASEB J. 1990, 4, 3284.
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    • See Supporting Information for details
    • See Supporting Information for details.
  • 39
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    • note
    • We first subjected the corresponding homoallylic homopropargylic alcohol to the resolution conditions of Taber (3 mass equiv AK, 60 °C, neat vinyl acetate) and observed that regardless of conversion, both the acetate and unreacted alcohol were racemic.
  • 40
    • 33746634508 scopus 로고    scopus 로고
    • Stereochemistry was confirmed by comparison of HPLC traces of this alcohol and of the identical substrate prepared previously. See ref 11a
    • Stereochemistry was confirmed by comparison of HPLC traces of this alcohol and of the identical substrate prepared previously. See ref 11a
  • 41
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    • note
    • Currently, this acetate is not of sufficient optical purity to be useful in the preparation of cryptophycin analogues. We are investigating solutions to this problem.
  • 43
    • 33746596777 scopus 로고    scopus 로고
    • Absolute stereochemistry was proven by X-ray analysis of 22
    • Absolute stereochemistry was proven by X-ray analysis of 22.
  • 44
    • 33746633695 scopus 로고    scopus 로고
    • For details on the synthesis of 11, see Supporting Information
    • For details on the synthesis of 11, see Supporting Information.
  • 45
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    • This product was a single disasteromer, suggesting it was not formed by RCM with the internal olefin, followed by ROM/RCM to form the macrocycle
    • This product was a single disasteromer, suggesting it was not formed by RCM with the internal olefin, followed by ROM/RCM to form the macrocycle.
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    • int = 0.0665). The data frames were integrated and scaled using the Denzo-SMN package (Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307-326.).
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    • Otwinowski, Z.1    Minor, W.2
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    • Bruker Analytical X-ray Systems Inc., Madison, WI
    • -3. CCDC-288364 (22) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/ data_request/cif.
    • (2001) SHELXTL-Windows NT. V6.12
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    • The configurations at the epoxide functionalities for 24maj and 24min have not yet been established
    • The configurations at the epoxide functionalities for 24maj and 24min have not yet been established.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.