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Volumn 76, Issue 2, 2008, Pages 1011-1016

A simple desymmetrization approach to the spiroxin framework

Author keywords

1,8 Dihydroxynaphthalene; Desymmetrization; Dimerization; Natural Product; Oxidative Cyclization

Indexed keywords


EID: 58149486285     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(N)70     Document Type: Article
Times cited : (15)

References (33)
  • 3
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    • For reviews on 1,8-dihydroxynaphtalene-derived natural products, see
    • For reviews on 1,8-dihydroxynaphtalene-derived natural products, see. Krohn K. Prog. Chem. Org. Nat. Prod. 85 (2003) 1
    • (2003) Prog. Chem. Org. Nat. Prod. , vol.85 , pp. 1
    • Krohn, K.1
  • 5
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    • Total synthesis of spiroxin C was reported
    • Total synthesis of spiroxin C was reported. Miyashita K., Sakai T., and Imanishi T. Org. Lett. 5 (2003) 2683
    • (2003) Org. Lett. , vol.5 , pp. 2683
    • Miyashita, K.1    Sakai, T.2    Imanishi, T.3
  • 7
    • 0000795285 scopus 로고
    • Structurally related 1,1'-binaphthyl-8,8'-diol has been used for chiral auxiliary and NMR chiral derivatizing reagent. For examples, see:
    • Structurally related 1,1'-binaphthyl-8,8'-diol has been used for chiral auxiliary and NMR chiral derivatizing reagent. For examples, see:. Fuji K., Kawabata T., Kuroda A., and Taga T. J. Org. Chem. 60 (1995) 1914
    • (1995) J. Org. Chem. , vol.60 , pp. 1914
    • Fuji, K.1    Kawabata, T.2    Kuroda, A.3    Taga, T.4
  • 12
    • 34248684093 scopus 로고    scopus 로고
    • Atropisomerization barriers of 1,1'-binaphthyl-8,8'-diol was determined to be 28.7 kcal/mol. Thus, axial-chirality of 1,1'-binaphthyl-4,4',8,8'-tetraol 3 is likely to be stable under the oxidative cyclization at room temperature (3 → 2).
    • Atropisomerization barriers of 1,1'-binaphthyl-8,8'-diol was determined to be 28.7 kcal/mol. Thus, axial-chirality of 1,1'-binaphthyl-4,4',8,8'-tetraol 3 is likely to be stable under the oxidative cyclization at room temperature (3 → 2). Tsubaki K., Hai D.T.T., Reddy V.K., Ohnishi H., Fuji K., and Kawabata K. Tetrahedron: Asymmetry 18 (2007) 1017
    • (2007) Tetrahedron: Asymmetry , vol.18 , pp. 1017
    • Tsubaki, K.1    Hai, D.T.T.2    Reddy, V.K.3    Ohnishi, H.4    Fuji, K.5    Kawabata, K.6
  • 20
    • 61349197271 scopus 로고    scopus 로고
    • The same oxidative reactions in trifluoroethanol were unsuccessful due to the low solubility of 3
    • The same oxidative reactions in trifluoroethanol were unsuccessful due to the low solubility of 3.
  • 27
    • 0031027260 scopus 로고    scopus 로고
    • For reviews on hypervalent iodine compounds, see:
    • For reviews on hypervalent iodine compounds, see:. Varvoglis A. Tetrahedron 53 (1997) 1179
    • (1997) Tetrahedron , vol.53 , pp. 1179
    • Varvoglis, A.1
  • 33
    • 61349120524 scopus 로고    scopus 로고
    • +) 362.0790, found 362.0788.
    • +) 362.0790, found 362.0788.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.