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Volumn 47, Issue 9, 2008, Pages 1777-1779

Total synthesis of the C-1027 chromophore core: Extremely facile enediyne formation through SmI2-mediated 1,2-elimination

Author keywords

Antitumor agents; Elimination; Enediynes; Natural products; Reduction

Indexed keywords

AROMATIC HYDROCARBONS; CHEMICAL REACTIONS; NUCLEIC ACIDS; ORGANIC ACIDS; SYNTHESIS (CHEMICAL);

EID: 41049115936     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704842     Document Type: Article
Times cited : (24)

References (36)
  • 4
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    • For a review on chromoprotein antibiotics and other enediyne natural products, see:, Eds, D. H. R. Barton, K. Nakanishi, Elsevier, Amsterdam
    • For a review on chromoprotein antibiotics and other enediyne natural products, see: Z. Xi, I. H. Goldberg in Comprehensive Natural Products Chemistry, Vol. 7 (Eds.: D. H. R. Barton, K. Nakanishi), Elsevier, Amsterdam, 1999, pp.553.
    • (1999) Comprehensive Natural Products Chemistry , vol.7 , pp. 553
    • Xi, Z.1    Goldberg, I.H.2
  • 5
    • 0000070605 scopus 로고
    • For reviews on the synthesis of enediyne compounds, see: a
    • For reviews on the synthesis of enediyne compounds, see: a) K. C. Nicolaou, W.-M. Dai, Angew. Chem. 1991, 103, 1453;
    • (1991) Angew. Chem , vol.103 , pp. 1453
    • Nicolaou, K.C.1    Dai, W.-M.2
  • 14
    • 34247867982 scopus 로고    scopus 로고
    • The total synthesis of the proposed structure of kedarcidin, a closely related enediyne chromophore, was completed recently by an elegant strategy: a F. Ren, P. C. Hogan, A. J. Anderson, A. G. Myers, J. Am. Chem. Soc. 2007, 129, 5381;
    • The total synthesis of the proposed structure of kedarcidin, a closely related enediyne chromophore, was completed recently by an elegant strategy: a) F. Ren, P. C. Hogan, A. J. Anderson, A. G. Myers, J. Am. Chem. Soc. 2007, 129, 5381;
  • 18
    • 0027300097 scopus 로고    scopus 로고
    • The phosphine-mediated elimination of thiocarbonate groups formed from cis 1,2-diols has been used to construct tenmembered-ring enediyne analogues: a M. F. Semmelhack, J. Gallagher, Tetrahedron Lett. 1993, 34, 4121;
    • The phosphine-mediated elimination of thiocarbonate groups formed from cis 1,2-diols has been used to construct tenmembered-ring enediyne analogues: a) M. F. Semmelhack, J. Gallagher, Tetrahedron Lett. 1993, 34, 4121;
  • 19
    • 0032985327 scopus 로고    scopus 로고
    • D. Crick, A. B. Pavlovic, D. J. Wink, Synth. Commun. 1999, 29, 359. However, this method was not applicable to our substrate with a trans 1,2-diol. Furthermore, the slow reaction rate is incompatible with the less stable nine-membered-ring enediyne systems.
    • b) D. Crick, A. B. Pavlovic, D. J. Wink, Synth. Commun. 1999, 29, 359. However, this method was not applicable to our substrate with a trans 1,2-diol. Furthermore, the slow reaction rate is incompatible with the less stable nine-membered-ring enediyne systems.
  • 21
    • 11844304180 scopus 로고    scopus 로고
    • For recent reviews of SmI2-mediated reactions, see: a J. M. Concellón, H. Rodríguez-Solla, Chem. Soc. Rev. 2004, 33, 599;
    • For recent reviews of SmI2-mediated reactions, see: a) J. M. Concellón, H. Rodríguez-Solla, Chem. Soc. Rev. 2004, 33, 599;
  • 24
    • 33947673321 scopus 로고    scopus 로고
    • For recent examples of related reactions, see: a
    • For recent examples of related reactions, see: a) J. Pospíš il, I. E. Markó, J. Am. Chem. Soc. 2007, 129, 3516;
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 3516
    • Pospíš il, J.1    Markó, I.E.2
  • 32
    • 0029113989 scopus 로고    scopus 로고
    • The rate of cycloaromatization of nine-membered enediyne ring systems depends on the solvent. Deuterated THF decelerated the concomitant cycloaromatization during the 1,2-elimination because of its kinetic isotope effect: K. Iida, M. Hirama, J. Am. Chem. Soc. 1995, 117, 8875; see also ref.[5].
    • The rate of cycloaromatization of nine-membered enediyne ring systems depends on the solvent. Deuterated THF decelerated the concomitant cycloaromatization during the 1,2-elimination because of its kinetic isotope effect: K. Iida, M. Hirama, J. Am. Chem. Soc. 1995, 117, 8875; see also ref.[5].
  • 35
  • 36
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    • The total synthesis of the maduropeptin aglycon was carried out by using the present strategy: K. Komano, S. Shimamura, M. Inoue, M. Hirama, J. Am. Chem. Soc. 2007, 129, 14184.
    • The total synthesis of the maduropeptin aglycon was carried out by using the present strategy: K. Komano, S. Shimamura, M. Inoue, M. Hirama, J. Am. Chem. Soc. 2007, 129, 14184.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.