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Volumn 49, Issue 4, 2008, Pages 650-653

Stereoselectivity in the organoiron-mediated synthesis of (±)-mesembrine

Author keywords

Asymmetric synthesis; Mesembrine; Organometallic electrophiles; Tricarbonyliron

Indexed keywords

ALKALOID DERIVATIVE; INDOLE DERIVATIVE; IRON COMPLEX; MESEMBRINE; ORGANOMETALLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

EID: 37549030187     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.11.137     Document Type: Article
Times cited : (21)

References (83)
  • 1
    • 8244226964 scopus 로고
    • Isolation from Sceletium tortuosum:
    • Isolation from Sceletium tortuosum:. Bodendorf K., and Krieger W. Archiv. Pharm. 290 (1957) 441-448
    • (1957) Archiv. Pharm. , vol.290 , pp. 441-448
    • Bodendorf, K.1    Krieger, W.2
  • 4
    • 37549010672 scopus 로고    scopus 로고
    • Gericke, N. P.; Van Wyk, B. E. World Patent 9,746,234, 1997
  • 11
    • 0000792906 scopus 로고    scopus 로고
    • Cordell G.A. (Ed), Academic Press, New York
    • Hoshino O. In: Cordell G.A. (Ed). The Alkaloids Vol. 51 (1998), Academic Press, New York 324-424
    • (1998) The Alkaloids , vol.51 , pp. 324-424
    • Hoshino, O.1
  • 12
    • 33947377017 scopus 로고    scopus 로고
    • the Amaryllidaceae alkaloids are still a rich source of new potentially biologically active target structures with substantial synthetic challenges:
    • the Amaryllidaceae alkaloids are still a rich source of new potentially biologically active target structures with substantial synthetic challenges:. Unver N. Phytochem. Rev. 6 (2007) 125-135
    • (2007) Phytochem. Rev. , vol.6 , pp. 125-135
    • Unver, N.1
  • 15
    • 33645985839 scopus 로고    scopus 로고
    • Examples of the biological activity of crinine: (inhibition of [3H]citalopram binding to the rat brain serotonin transporter)
    • Examples of the biological activity of crinine:. Elgorashi E.E., Stafford G.I., Jager A.K., and van Staden J. Plant. Med. 72 (2006) 470-473 (inhibition of [3H]citalopram binding to the rat brain serotonin transporter)
    • (2006) Plant. Med. , vol.72 , pp. 470-473
    • Elgorashi, E.E.1    Stafford, G.I.2    Jager, A.K.3    van Staden, J.4
  • 16
    • 37549044625 scopus 로고    scopus 로고
    • (anticholinesterase activity in Alzheimer's disease patients)
    • Orhan I., and Sener B. Acta Horticult. (2005) 678 (anticholinesterase activity in Alzheimer's disease patients)
    • (2005) Acta Horticult. , pp. 678
    • Orhan, I.1    Sener, B.2
  • 18
    • 37549055387 scopus 로고    scopus 로고
    • recent example (isolation from Pancratium tortuosum herb):
    • recent example (isolation from Pancratium tortuosum herb):. J. Pharm. Sci. 21 (2007) 61-68
    • (2007) J. Pharm. Sci. , vol.21 , pp. 61-68
  • 20
    • 0022606756 scopus 로고
    • Examples of the biological activity of maritidine: (clastogenic effect/mutagenic)
    • Examples of the biological activity of maritidine:. Cea G., Alarcon M., and Weigart G. Med. Sci. 14 (1986) 90 (clastogenic effect/mutagenic)
    • (1986) Med. Sci. , vol.14 , pp. 90
    • Cea, G.1    Alarcon, M.2    Weigart, G.3
  • 21
    • 37549064679 scopus 로고    scopus 로고
    • see also Ref. 7a.
  • 22
    • 34347406742 scopus 로고    scopus 로고
    • For examples, see:
    • For examples, see:. Nemoto H. Chem. Pharm. Bull. 55 (2007) 961-974
    • (2007) Chem. Pharm. Bull. , vol.55 , pp. 961-974
    • Nemoto, H.1
  • 24
    • 24944509594 scopus 로고    scopus 로고
    • (mesembrine)
    • Taber D.F., and He Y. J. Org. Chem. 70 (2005) 7711-7714 (mesembrine)
    • (2005) J. Org. Chem. , vol.70 , pp. 7711-7714
    • Taber, D.F.1    He, Y.2
  • 29
    • 37549052846 scopus 로고    scopus 로고
    • For our organoiron intermediate for crinine, see Ref. 3.
  • 33
    • 0032741056 scopus 로고    scopus 로고
    • galanthamine: (treatment of Alzheimer's disease)
    • galanthamine:. Weinstock M. CNS Drugs 11 (1999) 307-323 (treatment of Alzheimer's disease)
    • (1999) CNS Drugs , vol.11 , pp. 307-323
    • Weinstock, M.1
  • 37
    • 37549043867 scopus 로고    scopus 로고
    • Organometallic Complexes of Iron
    • 7: (b) For a survey of organoiron complexes, see:. Science of Synthesis. Lautens M. (Ed), Georg Theime Verlag, Stuttgart
    • 7: (b) For a survey of organoiron complexes, see:. Stephenson G.R. Organometallic Complexes of Iron. In: Lautens M. (Ed). Science of Synthesis. Houben-Weyl Methods of Molecular Transformations Vol. 1 (2001), Georg Theime Verlag, Stuttgart 745-886
    • (2001) Houben-Weyl Methods of Molecular Transformations , vol.1 , pp. 745-886
    • Stephenson, G.R.1
  • 38
    • 33646273060 scopus 로고
    • for earlier reviews of the applications of the cyclohexadienyliron series, see:
    • for earlier reviews of the applications of the cyclohexadienyliron series, see:. Pearson A.J. Acc. Chem. Res. 13 (1980) 463-469
    • (1980) Acc. Chem. Res. , vol.13 , pp. 463-469
    • Pearson, A.J.1
  • 44
    • 37549047946 scopus 로고    scopus 로고
    • note
    • We have developed one pot procedures to add the malononitrile nucleophile and then perform desilylation by addition of TBAF into the reactions mixture (conversion of 2b into 7) and for the reductive amination of the nitrile (conversion of 7 into 8), see Scheme 2.
  • 46
    • 37549040155 scopus 로고    scopus 로고
    • see also Ref. 17.
  • 48
    • 30544451537 scopus 로고    scopus 로고
    • For a discussion of chirality in such complexes, see:. Knochel P. (Ed), Wiley-VCH, Weinheim
    • For a discussion of chirality in such complexes, see:. Stephenson G.R. In: Knochel P. (Ed). Handbook of Functionalised Organometallics (2005), Wiley-VCH, Weinheim 569-626
    • (2005) Handbook of Functionalised Organometallics , pp. 569-626
    • Stephenson, G.R.1
  • 50
    • 37549031668 scopus 로고    scopus 로고
    • Older, J. E. J. PhD Thesis, University of East Anglia, 2001.
  • 51
    • 37549004339 scopus 로고    scopus 로고
    • Older, J. E. J. Stephenson, G. R. unpublished results; ees up to about 40% have been achieved with first generation chiral trityl analogues.
  • 55
    • 37549003611 scopus 로고    scopus 로고
    • note
    • The examples reported in this Letter were performed with racemic complexes.
  • 57
    • 37549019624 scopus 로고    scopus 로고
    • see also Ref. 4.
  • 58
    • 0006115320 scopus 로고
    • For the preparation of 3,4-dimethoxyphenyllithium from 3,4-dimethoxybromobenzene in THF at -78 °C, see:
    • For the preparation of 3,4-dimethoxyphenyllithium from 3,4-dimethoxybromobenzene in THF at -78 °C, see:. Meyers A.I., and Avila W.B. J. Org. Chem. 46 (1981) 3881-3886
    • (1981) J. Org. Chem. , vol.46 , pp. 3881-3886
    • Meyers, A.I.1    Avila, W.B.2
  • 59
    • 0001616965 scopus 로고
    • a procedure using 3,4-dimethoxyiodobenzene has also been reported:
    • a procedure using 3,4-dimethoxyiodobenzene has also been reported:. Capparelli M.P., DeSchepper R.E., and Swenton J.S. J. Org. Chem. 52 (1987) 4953-4957
    • (1987) J. Org. Chem. , vol.52 , pp. 4953-4957
    • Capparelli, M.P.1    DeSchepper, R.E.2    Swenton, J.S.3
  • 60
    • 37549038593 scopus 로고    scopus 로고
    • note
    • After 5 min to form the aryllithium reagent, the reaction mixture was cooled to -78 °C before addition of the trimethylsilyl chloride.
  • 66
    • 37549005951 scopus 로고    scopus 로고
    • see also Ref. 3.
  • 76
    • 37549067686 scopus 로고    scopus 로고
    • note
    • For a discussion of ipso and ω addition to multihapto π complexes, see Ref. 18. For the ω directing nature of aryl substituents on cyclohexadienyliron complexes, see Ref. 3. In this case, the presence of the 4-OMe group helps overcome the natural ω selectivity and promote the ipso pathway (ipso relative to the position of the arene). This is because the C(4) OMe is also ω directing (see Ref. 31), and the two control effects are opposed (for definitions of the terms 'mutually reinforcing' and 'opposed' in the context of nucleophile addition to multiply substituted ligands, see Ref. 18).
  • 77
    • 0037647990 scopus 로고
    • For examples with opposed Me and OMe groups:
    • For examples with opposed Me and OMe groups:. Pearson A.J., and Perrior T.R. J. Organomet. Chem. 285 (1985) 253-265
    • (1985) J. Organomet. Chem. , vol.285 , pp. 253-265
    • Pearson, A.J.1    Perrior, T.R.2
  • 81
    • 37049096977 scopus 로고
    • We used a similar approach towards the terpene tridachione:
    • We used a similar approach towards the terpene tridachione:. Stephenson G.R. J. Chem. Soc., Perkin Trans. 1 (1982) 2449-2456
    • (1982) J. Chem. Soc., Perkin Trans. 1 , pp. 2449-2456
    • Stephenson, G.R.1
  • 83
    • 37549039779 scopus 로고    scopus 로고
    • Roe, C.; Stephenson, G. R. Org. Lett., submitted for publication.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.