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Volumn 52, Issue 5, 2011, Pages 581-583

Total synthesis of (+)-eupomatilone 2 via asymmetric [2,3]-Wittig rearrangement of highly oxygenated biphenylmethyl ethers

Author keywords

2,3 Wittig rearrangement; Asymmetric synthesis; Bis(oxazoline) ligand; Natural product

Indexed keywords

BASE; BIPHENYLMETHYL ETHER; BIS(OXAZOLINE)LIGAND; ETHER DERIVATIVE; EUPOMATILONE 2; LITHIUM DERIVATIVE; N BUTYLLITHIUM; NATURAL PRODUCT; OXAZOLINE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG;

EID: 78651081145     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.126     Document Type: Article
Times cited : (16)

References (35)
  • 16
    • 33845550583 scopus 로고
    • The relative relationship was able to speculate from the coupling constants between the C1- and C2-methin protons. The values of syn-isomers are ranged around 4 Hz. Instead, those of the corresponding anti-isomers exhibit the larger value around 8 Hz. A similar empirical rule was also reported by Nakai
    • The relative relationship was able to speculate from the coupling constants between the C1- and C2-methin protons. The values of syn-isomers are ranged around 4 Hz. Instead, those of the corresponding anti-isomers exhibit the larger value around 8 Hz. A similar empirical rule was also reported by Nakai, see; Mikami, K.; Kimura, Y.; Kishi, N.; Nakai, T. J. Org. Chem. 1983, 48, 279-281.
    • (1983) T. J. Org. Chem. , vol.48 , pp. 279-281
    • Mikami, K.1    Kimura, Y.2    Kishi, N.3    Nakai4
  • 18
    • 33645791244 scopus 로고    scopus 로고
    • For asymmetric [2,3]-Wittig rearrangement employing an external chiral ligand, see: K. Tomooka Chem. Organolithium Compd. 2 2004 749 828
    • (2004) Chem. Organolithium Compd. , vol.2 , pp. 749-828
    • Tomooka, K.1
  • 30
    • 78651064609 scopus 로고    scopus 로고
    • note
    • +.
  • 34
    • 78651099311 scopus 로고    scopus 로고
    • The enantiomeric excess of the synthetic (+)-eupomatilone 2 was confirmed as 89% ee by chiral HPLC (Column: CHIRALPAK AD-H, solvent: hexane-i-PrOH = 9:1, flow rate: 1 mL/min)
    • The enantiomeric excess of the synthetic (+)-eupomatilone 2 was confirmed as 89% ee by chiral HPLC (Column: CHIRALPAK AD-H, solvent: hexane-i-PrOH = 9:1, flow rate: 1 mL/min).
  • 35
    • 78651068353 scopus 로고    scopus 로고
    • note
    • +.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.