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Volumn 43, Issue 27, 2004, Pages 3601-3605

Total synthesis of the salicylate enamide macrolide oximidine III: Application of relay ring-closing metathesis

Author keywords

Antitumor agents; Enamides; Natural products; Ring closing metathesis; Vinyl iodides

Indexed keywords

HYDROGEN; POLYMERIZATION; STEREOCHEMISTRY; SUBSTRATES; SYNTHESIS (CHEMICAL);

EID: 4143108202     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200460042     Document Type: Article
Times cited : (76)

References (44)
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    • b) for a recent review of syntheses and SAR studies, see: L. Yet, Chem. Rev. 2003, 103, 4283.
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    • Recent reviews: a) A. Fürstner, Angew. Chem. 2000, 112, 3140; Angew. Chem. Int. Ed. 2000, 39, 3012;
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 3012
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    • For an example of allylic substitution effects on reaction rates of RCM, see: T. R. Hoye, H. Zhao, Org. Lett. 1999, 1, 1123.
    • (1999) Org. Lett. , vol.1 , pp. 1123
    • Hoye, T.R.1    Zhao, H.2
  • 26
    • 0030857814 scopus 로고    scopus 로고
    • d) for another application of a "relay" entity in the assembly of reacting sites in RCM, see: A. Fürstner, K. Langemann, Synthesis 1997, 792.
    • (1997) Synthesis , pp. 792
    • Fürstner, A.1    Langemann, K.2
  • 29
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    • note
    • Use of a sterically demanding TBS protecting group on the secondary alcohol resulted in low diastereoselectivity of the Sharpless asymmetric epoxidation (4:1).
  • 32
    • 4544273147 scopus 로고    scopus 로고
    • note
    • Use of the Grubbs first-generation catalyst led to the corresponding by-products 6 (Scheme 2).
  • 41
    • 0009642251 scopus 로고
    • b) for use of iodoalkyl phenyl sulfone reagents in free radical reactions, see: P. Jankowski, M. Masnyk, J. Wicha, Synlett 1995, 866.
    • (1995) Synlett , pp. 866
    • Jankowski, P.1    Masnyk, M.2    Wicha, J.3
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    • note
    • 1H NMR analysis.
  • 43
    • 4544284526 scopus 로고    scopus 로고
    • note
    • In our synthesis of oximidine II (ref. [5a]), we utilized a silylated phenol substrate treated with base and amide (2 equiv each) in a copper-mediated coupling to effect both silyl ether deprotection and enamide formation. However, use of excess base and amide in the syntheses described herein led to significant decomposition of the sensitive vinyl epoxide moiety.
  • 44
    • 4544278387 scopus 로고    scopus 로고
    • note
    • V-ATPase activity was determined as described in the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.