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Volumn 70, Issue 8, 2005, Pages 3277-3280

A novel formal total synthesis of cephalotaxine

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AROMATIC COMPOUNDS; KETONES; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL);

EID: 17444380057     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048046o     Document Type: Article
Times cited : (28)

References (24)
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    • Brossi, A., Ed.; Academic Press: New York
    • For reviews, see: (a) Huarig, L.; Xue, Z. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1984; Vol. 23, pp 157-226. (b) Jalil Miah, M. A.; Hudlicky, T.; Reed, J. W. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1998; Vol. 51, pp 199-269.
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    • For recent synthesis of CET, see: (a) Planas, L.; Perard-Viret, J.; Royer, J. J. Org. Chem. 2004, 69, 3087. (b) Li, W.-D. Z.; Wang, Y.-Q. Org. Lett. 2003, 5, 2931 and references therein, (c) Koseki, Y.; Sato, H.; Watanabe, Y.; Nagasaka, T. Org. Lett. 2002, 4, 885.
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    • and references therein
    • For recent synthesis of CET, see: (a) Planas, L.; Perard-Viret, J.; Royer, J. J. Org. Chem. 2004, 69, 3087. (b) Li, W.-D. Z.; Wang, Y.-Q. Org. Lett. 2003, 5, 2931 and references therein, (c) Koseki, Y.; Sato, H.; Watanabe, Y.; Nagasaka, T. Org. Lett. 2002, 4, 885.
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    • See Experimental Section for detailed procedures
    • See Experimental Section for detailed procedures.
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    • Ph.D. Thesis (Novel Total Synthesis of Cephalotaxine), Lanzhou University
    • Wang, Y.-Q. Ph.D. Thesis (Novel Total Synthesis of Cephalotaxine), Lanzhou University, 2003.
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    • note
    • 2 (all data) = 0.1428. See Supporting Information for detailed X-ray crystallographic data.
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    • Cf.: (a) Weinreb, S. M.; Auerbach, J. J. Am. Chem. Soc. 1975, 97, 2503. (b) Weinreb, S. M.; Semmelhack, M. F. Acc. Chem. Res. 1975, 8, 158. (c) Weinstein, B.; Craig, A. R. J. Org. Chem. 1976, 41, 875. (d) Tse, I.; Snieckus, V. J. Chem. Soc., Chem. Commun. 1976, 505. (e) Fang, F. G.; Maier, M. E.; Danishefsky, S. J.; Schulte, G. J. Org. Chem. 1990, 55, 831.
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    • Cf.: (a) Weinreb, S. M.; Auerbach, J. J. Am. Chem. Soc. 1975, 97, 2503. (b) Weinreb, S. M.; Semmelhack, M. F. Acc. Chem. Res. 1975, 8, 158. (c) Weinstein, B.; Craig, A. R. J. Org. Chem. 1976, 41, 875. (d) Tse, I.; Snieckus, V. J. Chem. Soc., Chem. Commun. 1976, 505. (e) Fang, F. G.; Maier, M. E.; Danishefsky, S. J.; Schulte, G. J. Org. Chem. 1990, 55, 831.
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    • note
    • This result would exclude the possibility that Dolby's cyclization-isomerization of 7 → 14 may proceed via compound 5 as an intermediate.
  • 23
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    • note
    • The chemical yields in this work will be subjected to further optimization.
  • 24
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    • note
    • For General Experimental Procedures see the Supporting Information of ref 2b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.