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Volumn 49, Issue 17, 2008, Pages 2722-2725

An efficient method for construction of tetrahydroisoquinoline skeleton via double cyclization process using ortho-vinylbenzaldehydes and amino alcohols: application to the synthesis of (S)-cryptostyline II

Author keywords

(S) Cryptostyline II; 6 Azaelectrocyclization; Double cyclization process; Tetrahydroisoquinoline

Indexed keywords

ALDEHYDE; ALKALOID; AMINOALCOHOL; CRYPTOSTYLINE DERIVATIVE; ISOQUINOLINE DERIVATIVE; PROPANOL; TETRAHYDROISOQUINOLINE; UNCLASSIFIED DRUG;

EID: 40949099425     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.152     Document Type: Article
Times cited : (22)

References (45)
  • 1
    • 0000938909 scopus 로고
    • For reviews, see:. Trost B.M., and Fleming I. (Eds), Pergamon, Oxford, UK
    • For reviews, see:. Okamura W.H., and de Lera A.R. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford, UK 699-750
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 699-750
    • Okamura, W.H.1    de Lera, A.R.2
  • 3
    • 33845280286 scopus 로고
    • For leading references on electrocyclic ring-closures involving 1-azatrienes, see:
    • For leading references on electrocyclic ring-closures involving 1-azatrienes, see:. Okamura W.H., de Lera A.R., and Reischl W. J. Am. Chem. Soc. 110 (1988) 4462-4464
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 4462-4464
    • Okamura, W.H.1    de Lera, A.R.2    Reischl, W.3
  • 22
    • 3543059896 scopus 로고    scopus 로고
    • For reviews on the asymmetric synthesis of isoquinolines, see:
    • For reviews on the asymmetric synthesis of isoquinolines, see:. Chrzanowska M., and Rozwadowska M.D. Chem. Rev. 104 (2004) 3341-3370
    • (2004) Chem. Rev. , vol.104 , pp. 3341-3370
    • Chrzanowska, M.1    Rozwadowska, M.D.2
  • 23
    • 5744254384 scopus 로고    scopus 로고
    • and references therein
    • Bracca A.B.J., and Kaufman T.S. Tetrahedron 60 (2004) 10575-10610 and references therein
    • (2004) Tetrahedron , vol.60 , pp. 10575-10610
    • Bracca, A.B.J.1    Kaufman, T.S.2
  • 24
    • 1542298884 scopus 로고    scopus 로고
    • For recent examples of 6π-azaelectrocyclization for synthesis of benzene-fused heterocycles, see:
    • For recent examples of 6π-azaelectrocyclization for synthesis of benzene-fused heterocycles, see:. Kuwabara N., Hayashi H., Hiramatsu N., Choshi T., Kumemura T., Nobuhiro J., and Hibino S. Tetrahedron 60 (2004) 2943-2952
    • (2004) Tetrahedron , vol.60 , pp. 2943-2952
    • Kuwabara, N.1    Hayashi, H.2    Hiramatsu, N.3    Choshi, T.4    Kumemura, T.5    Nobuhiro, J.6    Hibino, S.7
  • 34
    • 40949151272 scopus 로고    scopus 로고
    • Several asymmetric syntheses of cryptostyline II have been reported, see: Ref. 10b.
    • Several asymmetric syntheses of cryptostyline II have been reported, see: Ref. 10b.
  • 41
    • 40949140280 scopus 로고    scopus 로고
    • note
    • 4 and evaporated to leave the crude product, which was purified by column chromatography (silica gel, hexane/AcOEt = 3/1 as eluent) to give 11 (2.65 g, 13.8 mmol) in 95% yield as a colorless solid.
  • 42
    • 40949140687 scopus 로고    scopus 로고
    • note
    • 3: C, 73.29; H, 6.80; N, 4.50. Found: C, 73.10; H, 6.76; N, 4.59.
  • 44
    • 40949152546 scopus 로고    scopus 로고
    • note
    • 5: C, 72.14; H, 6.95; N, 3.12. Found: C, 72.01; H, 7.10; N, 2.95.
  • 45
    • 40949116437 scopus 로고    scopus 로고
    • note
    • 14


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.