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Volumn 4, Issue 1, 2002, Pages 127-129

Concise synthesis and transannular inverse electron demand Diels-Alder reaction of [3](3,6)pyridazino[3](1,3)indolophane. Rapid access to a pentacyclic indoloid system

Author keywords

[No Author keywords available]

Indexed keywords

(3)(3,6)PYRIDAZINO(3)(1,3)INDOLOPHANE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; INDOLE DERIVATIVE; POLYCYCLIC HYDROCARBON; PYRIDAZINE DERIVATIVE;

EID: 0037050486     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol017014+     Document Type: Article
Times cited : (55)

References (61)
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    • (b) Cyclophanes; Keehn, P. M., Rosenfeld, S. M., Eds.; Academic Press: New York, 1983; Vols. 1, 2.
    • (1983) Cyclophanes , vol.1-2
    • Keehn, P.M.1    Rosenfeld, S.M.2
  • 4
    • 0003825877 scopus 로고
    • Royal Society of Chemistry: London
    • (d) Diederich, F. N. Cyclophanes; Royal Society of Chemistry: London, 1991.
    • (1991) Cyclophanes
    • Diederich, F.N.1
  • 8
    • 0345294097 scopus 로고    scopus 로고
    • Schmalz, H.-G., Ed.; Wiley-VCH: Weinheim, Germany
    • (c) Bodwell, G. J. In Organic Synthesis Highlights IV; Schmalz, H.-G., Ed.; Wiley-VCH: Weinheim, Germany, 2000.
    • (2000) Organic Synthesis Highlights , vol.4
    • Bodwell, G.J.1
  • 13
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    • Pyrrolophanes have served as key intermediates in the synthesis of roseophylin: (a) Harrington, P. E.; Tius, M. A. J. Am. Chem. Soc. 2001, 123, 8509-8514.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 8509-8514
    • Harrington, P.E.1    Tius, M.A.2
  • 16
    • 0033515731 scopus 로고    scopus 로고
    • Furanophanes and their transannular Diels-Alder reactions have been reported in synthetic approaches to chanticin; (d) Toró, A.; Wang, Y.; Deslongchamps, P. Tetrahedron Lett. 1999, 40, 2765-2768.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2765-2768
    • Toró, A.1    Wang, Y.2    Deslongchamps, P.3
  • 32
    • 0007586467 scopus 로고
    • For a transannular Diels-Alder reaction of a [3.3]cyclophane see: (b) Longone, D. T.; Gladysz, J. A. Tetrahedron Lett. 1976, 17, 4559-4562.
    • (1976) Tetrahedron Lett. , vol.17 , pp. 4559-4562
    • Longone, D.T.1    Gladysz, J.A.2
  • 38
    • 0043096203 scopus 로고    scopus 로고
    • note
    • Details of this unsuccessful route will be described in a forthcoming publication.
  • 54
    • 0042094370 scopus 로고    scopus 로고
    • note
    • For this cyclophane, the term endo is used to describe conformers in which the nitrogen atoms of the pyridazine ring are situated underneath the indole system. The term exo is used to describe conformers in which the nitrogen atoms of the pyridazine ring are situated away from the indole system, as shown in Scheme 2.
  • 56
    • 0041593375 scopus 로고    scopus 로고
    • note
    • Intermediate 9 is the result of an intramolecular IEDDA reaction from an exo conformation. Reaction from an endo conformation would afford a different diastereoisomer, but this would also produce (±)-10 upon expulsion of nitrogen.
  • 58
    • 0034273688 scopus 로고    scopus 로고
    • (a) For a review of strychnine syntheses, see: Bonjoch, J.; Solé, D. Chem. Rev. 2000, 100, 3455-3482.
    • (2000) Chem. Rev. , vol.100 , pp. 3455-3482
    • Bonjoch, J.1    Solé, D.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.