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Volumn 7, Issue 11, 2005, Pages 2221-2224

Enantioselective access to isoquinuclidines by tropenone desymmetrization and homoallylic radical rearrangement: Synthesis of (+)-ibogamine

Author keywords

[No Author keywords available]

Indexed keywords

ALKANONE; ALLYL COMPOUND; AMIDE; IBOGAMINE; NITROGEN; TIN DERIVATIVE;

EID: 20444471536     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050627s     Document Type: Article
Times cited : (37)

References (35)
  • 2
    • 0036962028 scopus 로고    scopus 로고
    • (b) For a recent synthesis of ibogamine 1, see: White, J. D.; Choi, Y. Helv. Chem. Acta 2002, 85, 4306-4327.
    • (2002) Helv. Chem. Acta , vol.85 , pp. 4306-4327
    • White, J.D.1    Choi, Y.2
  • 11
    • 0029880916 scopus 로고    scopus 로고
    • For a related homoallylic radical rearrangement of a tropane derivative leading to a 6-azabicyclo[3.2.1]octane, see: Rigby, J. H.; Pigge, F. C. Tetrahedron Lett. 1996, 37, 2201-2204.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2201-2204
    • Rigby, J.H.1    Pigge, F.C.2
  • 16
    • 20444493348 scopus 로고    scopus 로고
    • CDCC 265105 available at http://www.ccdc.cam.ac.uk.
  • 18
    • 20444473928 scopus 로고    scopus 로고
    • note
    • Careful control of the temperature is necessary to avoid competitive removal of the bromine substituent, followed by further reduction. Very slow warming up of the cooling bath must be performed with a critical stage around -15°C where most of the reduction occurs.
  • 19
    • 20444490930 scopus 로고    scopus 로고
    • CDCC 265106 available at http://www.ccdc.cam.ac.uk.
  • 25
    • 20444435676 scopus 로고    scopus 로고
    • See Supporting Information
    • See Supporting Information.
  • 26
    • 20444504908 scopus 로고    scopus 로고
    • CDCC 265107 available at http://www.cdcc.cam.ac.uk.
  • 27
    • 20444480374 scopus 로고    scopus 로고
    • CDCC 265108 available at http://www.ccdc.cam.ac.uk.
  • 28
    • 20444448652 scopus 로고    scopus 로고
    • note
    • In light of our results, Prof. Krow reassessed the NMR experiments originally used to assign 12 and 7-epi-12 in ref 17 and agrees that the C-7 stereochemical assignments should be reversed.
  • 34
    • 0000174970 scopus 로고
    • Ethyl epimer of 1 has also been previously prepared using Trost's cyclization procedure, in 20% yield, see: Tomisawa, H.; Hongo, H.; Kato, H.: Sato, K.; Fujita, R. Heterocycles 1981, 16, 1947-1950.
    • (1981) Heterocycles , vol.16 , pp. 1947-1950
    • Tomisawa, H.1    Hongo, H.2    Kato, H.3    Sato, K.4    Fujita, R.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.