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Volumn 19, Issue 16, 2008, Pages 1978-1983

Enantioselective total synthesis of the tricyclic 9-oxabispidine (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.02,7]tridecane

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLIC 9 OXABISPIDINE; EPICHLOROHYDRIN; TRICYCLIC 9 OXABISPIDINE 11 METHYL 13 OXA 7,11 DIAZATRICYCLO[7.3.1.0 2,7]TRIDECANE; TRIDECANE; UNCLASSIFIED DRUG;

EID: 50649114391     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.08.002     Document Type: Article
Times cited : (13)

References (59)
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    • (-)-Sparteine (-)-1, also known as lupinidine, was first isolated in 1851:
    • (-)-Sparteine (-)-1, also known as lupinidine, was first isolated in 1851:. Stenhouse J. Ann. Chem. Pharm. 78 (1851) 1-30
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  • 3
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    • The structure of (-)-1 was elucidated in 1933
    • The structure of (-)-1 was elucidated in 1933. Clemo G.R., and Raper R. J. Chem. Soc. (1933) 644-645
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  • 11
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  • 13
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    • Sorger, K.; Petersen, H.; Stohrer, J. U.S. Patent 6,924,386, 2005.
    • Sorger, K.; Petersen, H.; Stohrer, J. U.S. Patent 6,924,386, 2005.
  • 14
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    • For earlier (-)-sparteine-mediated Reformatsky reactions see:
    • For earlier (-)-sparteine-mediated Reformatsky reactions see:. Guetté M., Capillon J., and Guetté J.-P. Tetrahedron 29 (1973) 3659-3667
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  • 29
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    • (+)-Sparteine (+)-1, also known as pachycarpine, was first isolated in 1933 from Sophora pachycarpa C. A. Mey:
    • (+)-Sparteine (+)-1, also known as pachycarpine, was first isolated in 1933 from Sophora pachycarpa C. A. Mey:. Orechoff A., Rabinowitch M., and Konowalowa R. Ber. Dtsch. Chem. Ges. 66 (1933) 621-625
    • (1933) Ber. Dtsch. Chem. Ges. , vol.66 , pp. 621-625
    • Orechoff, A.1    Rabinowitch, M.2    Konowalowa, R.3
  • 30
    • 0024697050 scopus 로고
    • It can also be prepared by reduction and resolution of the naturally occurring alkaloid rac-lupanine (rac-10-oxosparteine), see:
    • It can also be prepared by reduction and resolution of the naturally occurring alkaloid rac-lupanine (rac-10-oxosparteine), see:. Ebner T., Eichelbaum M., Fischer P., and Meese C.O. Arch. Pharm. (Weinheim) 322 (1989) 399-403
    • (1989) Arch. Pharm. (Weinheim) , vol.322 , pp. 399-403
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  • 33
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    • For the synthesis of N-alkyl derivatives of 2 from 3, see:
    • For the synthesis of N-alkyl derivatives of 2 from 3, see:. Dearden M.J., McGrath M.J., and O'Brien P. J. Org. Chem. 69 (2004) 5789-5792
    • (2004) J. Org. Chem. , vol.69 , pp. 5789-5792
    • Dearden, M.J.1    McGrath, M.J.2    O'Brien, P.3
  • 41
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    • For the stereoselective synthesis of other bispidines possessing a chirally modified core, see:
    • For the stereoselective synthesis of other bispidines possessing a chirally modified core, see:. Smith B.T., Wendt J.A., and Aubé J. Org. Lett. 4 (2002) 2577-2579
    • (2002) Org. Lett. , vol.4 , pp. 2577-2579
    • Smith, B.T.1    Wendt, J.A.2    Aubé, J.3
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    • note
    • There is a single abstract of a lecture by Gill et al. held at the 232nd ACS National Meeting, in which an enantioselective route to 6 and some other bicyclic 9-oxabispidines of type 4 is sketched. However, no yields or characterization data are given, see: Gill, D. M.; Holness, H.; Keegan, P. S. Abstracts of Papers, 232nd ACS National Meeting, San Francisco, 2006.
  • 47
    • 50649108241 scopus 로고    scopus 로고
    • note
    • It should be noted that due to the additional oxygen atom in 4, a competing N,O-complexation of metals might occur. Preliminary quantum chemical calculations, however, showed such a complexation to be strongly disfavored as compared to the N,N-complexation of metals.
  • 57
    • 50649091877 scopus 로고    scopus 로고
    • Ref. 16b.
    • Ref. 16b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.