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Volumn 133, Issue 20, 2011, Pages 7704-7707

Total synthesis of (±)-cycloclavine and (±)-5-epi- cycloclavine

Author keywords

[No Author keywords available]

Indexed keywords

[4 + 2] CYCLOADDITION; BUILDING BLOCKES; DIELS-ALDER; DIELS-ALDER REACTION; DIENOPHILES; INDOLE ALKALOIDS; INDOLE ANNULATION; KEY FEATURE; METHYLENECYCLOPROPANES; NATURALLY OCCURRING; NOVEL ROUTE; RAPID CONSTRUCTION; STEREO-SELECTIVE; TOTAL SYNTHESIS;

EID: 79957687758     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja2026882     Document Type: Article
Times cited : (128)

References (30)
  • 6
    • 57549092044 scopus 로고    scopus 로고
    • For pioneering applications of the IMDAF cycloaddition to natural product synthesis, see: J. Org. Chem. 2011, 76, 2753 and references cited therein
    • Petronijević, F.; Timmons, C.; Cuzzupe, A.; Wipf, P. Chem. Commun. 2009, 1, 104 For pioneering applications of the IMDAF cycloaddition to natural product synthesis, see: Boonsompat, J. and Padwa, A. J. Org. Chem. 2011, 76, 2753 and references cited therein
    • (2009) Chem. Commun. , vol.1 , pp. 104
    • Petronijević, F.1    Timmons, C.2    Cuzzupe, A.3    Wipf, P.4    Boonsompat, J.5    Padwa, A.6
  • 13
    • 79957699094 scopus 로고    scopus 로고
    • 2) failed to provide the desired product, instead favoring cyclopropane ring opening
    • 2) failed to provide the desired product, instead favoring cyclopropane ring opening.
  • 17
    • 84987305286 scopus 로고
    • For the formation and use in Diels-Alder reactions of amino dienes, see
    • For the formation and use in Diels-Alder reactions of amino dienes, see: Oppolzer, W.; Fröstl, W. Helv. Chim. Acta 1975, 58, 590
    • (1975) Helv. Chim. Acta , vol.58 , pp. 590
    • Oppolzer, W.1    Fröstl, W.2
  • 22
    • 79957751363 scopus 로고    scopus 로고
    • Transition states were identified using an RHF/6-311G* transition state search in Spartan 10 (Wavefunction, Inc., Irvine, CA)
    • Transition states were identified using an RHF/6-311G* transition state search in Spartan 10 (Wavefunction, Inc., Irvine, CA).
  • 25
    • 79957694569 scopus 로고    scopus 로고
    • 2 239.1548, found 239.1572
    • 2 239.1548, found 239.1572.
  • 26
    • 0030576867 scopus 로고    scopus 로고
    • In a few cases, unsubstituted methylenecyclopropane and other simple derivatives, such as perfluoromethylenecyclopropane, 2,2- difluoromethylenecyclopropane, and methyl 2-chloro-2-cyclopropylidene acetate, have been used in intermolecular [4 + 2] cycloadditions, (20) but to the best of our knowledge there is only one prior report of an intramolecular, high pressure Diels-Alder variant with this strain-activated dienophile
    • In a few cases, unsubstituted methylenecyclopropane and other simple derivatives, such as perfluoromethylenecyclopropane, 2,2- difluoromethylenecyclopropane, and methyl 2-chloro-2-cyclopropylidene acetate, have been used in intermolecular [4 + 2] cycloadditions, (20) but to the best of our knowledge there is only one prior report of an intramolecular, high pressure Diels-Alder variant with this strain-activated dienophile: Heiner, T.; Kozhushkov, S. I.; Noltemeyer, M.; Haumann, T.; Boese, R.; De Meijere, A. Tetrahedron 1996, 52, 12185
    • (1996) Tetrahedron , vol.52 , pp. 12185
    • Heiner, T.1    Kozhushkov, S.I.2    Noltemeyer, M.3    Haumann, T.4    Boese, R.5    De Meijere, A.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.