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Volumn 16, Issue 15, 2010, Pages 4623-4628

A concise total synthesis of (+)-tetrabenazine and (+)-α- dihydrotetrabenazine

Author keywords

Bentazines; Claisen rearrangement; Rearrangement; Total synthesis

Indexed keywords

ACTIVE METABOLITES; ASYMMETRIC TOTAL SYNTHESIS; AZA-CLAISEN REARRANGEMENT; CARBON FRAMEWORK; CLAISEN REARRANGEMENT; DIHYDROTETRABENAZINE; HUNTINGTON'S DISEASE; STEREOGENIC CENTERS; SYNTHETIC ROUTES; TOTAL SYNTHESIS;

EID: 77950818724     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200902591     Document Type: Article
Times cited : (38)

References (53)
  • 2
    • 33846225133 scopus 로고    scopus 로고
    • b) F. O. Walker, Lancet 2007, 369,218-228.
    • (2007) Lancet , vol.369 , pp. 218-228
    • Walker, F.O.1
  • 3
    • 84891924243 scopus 로고    scopus 로고
    • www.euro-hd.net
  • 4
    • 84891906314 scopus 로고    scopus 로고
    • a) www.fda.gov
  • 7
    • 33645798913 scopus 로고    scopus 로고
    • Huntington study group
    • b) Huntington study group. Neurology 2006, 66, 366-372.
    • (2006) Neurology , vol.66 , pp. 366-372
  • 25
    • 0033521185 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1999. 38, 3545-3547;
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 3545-3547
  • 27
    • 0006077638 scopus 로고    scopus 로고
    • For a review on the synthesis of medium-sized lactams, see: U. Nubbemeyer, Top. Curr. Chem. 2001. 216. 125-196.
    • (2001) Top. Curr. Chem. , vol.216 , pp. 125-196
    • Nubbemeyer, U.1
  • 28
    • 0000653676 scopus 로고
    • For representative transannulalion approaches Io related skeletons, see: a) E. D. Edstrom, J. Am. Chem. Soc. 1991, 113, 6690-6692;
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 6690-6692
    • Edstrom, E.D.1
  • 33
    • 0000814530 scopus 로고
    • (Eds: B. M. Trost, I. Fleming), Pergamon Press, Oxford
    • T. K. M. Shing. In Comprehensive Organic Synthesis Vol.7 (Eds: B. M. Trost, I. Fleming), Pergamon Press, Oxford, 1991, pp. 703-716.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 703-716
    • Shing, T.K.M.1
  • 34
    • 84891913274 scopus 로고    scopus 로고
    • 1H coupling constants. See ref. [15]
    • 1H coupling constants. See ref. [15].
  • 37
    • 0032731884 scopus 로고    scopus 로고
    • Bellus-Claisen rearrangements in the presence of various metal cations and ligands have been reported by D. W. C MacMillan's group. See a) T. P. Yoon, V. M. Dong, D. W. C MacMillan, J. Am. Chem. Soc. 1999, 121, 9726-9727;
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 9726-9727
    • Yoon, T.P.1    Dong, V.M.2    MacMillan, D.W.C.3
  • 39
    • 0001280525 scopus 로고
    • One example of a Claisen rearrangement of an ester with the aid of 2-mesitylMgBr has been reported. See R.T. Arnold. S. Searles Jr.,J. Am. Chem. Soc. 1949. 71. 1150-1151.
    • (1949) J. Am. Chem. Soc. , vol.71 , pp. 1150-1151
    • Arnold, R.T.1    Searles Jr., S.2
  • 40
    • 34247229204 scopus 로고    scopus 로고
    • Recently, carbomagnesiation of an ynamide moiety with use of a Grignard reagent as a nucleophile and concomitant ACR has been reported. See: H. Yasui. H. Yorimitsu. K. Oshima, Chem. Lett. 2007, 56. 32-33.
    • (2007) Chem. Lett. , vol.56 , pp. 32-33
    • Yasui, H.1    Yorimitsu, H.2    Oshima, K.3
  • 41
    • 3543059896 scopus 로고    scopus 로고
    • For recent reviews on the synthesis of benzoisoquinolizidines, see a) M. Chrzanowska. M. D. Rozwadowska. Chem. Rev. 2004, 104, 3341-3370;
    • (2004) Chem. Rev. , vol.104 , pp. 3341-3370
    • Chrzanowska, M.1    Rozwadowska, M.D.2
  • 42
    • 0000415230 scopus 로고    scopus 로고
    • For selected examples, see b) L. F. Tietze, Y. Zhou, Angew. Chem. 1999, 111, 2076-2078:
    • (1999) Angew. Chem. , vol.111 , pp. 2076-2078
    • Tietze, L.F.1    Zhou, Y.2
  • 43
    • 0033549505 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 1999, 38. 2045-2047:
    • (1999) Angew. Chem. Int. Ed. , vol.38 , pp. 2045-2047
  • 50
    • 84891949948 scopus 로고    scopus 로고
    • For the mechanism of this conversion a two-step process (initial protonation of the olefin to generate an O-methylated quinine and capture of the resulting carbocation by amide) is also possible. A mechanistic study is in progress
    • For the mechanism of this conversion a two-step process (initial protonation of the olefin to generate an O-methylated quinine and capture of the resulting carbocation by amide) is also possible. A mechanistic study is in progress.
  • 52
    • 84891913366 scopus 로고    scopus 로고
    • D = +53.5 (c= 1.60. MeOH))
    • D = +53.5 (c= 1.60. MeOH)).
  • 53
    • 84891955519 scopus 로고    scopus 로고
    • Two TBZ molecules were co-crystallized and one TBZ molecule is shown. For details see the Supporting Information
    • Two TBZ molecules were co-crystallized and one TBZ molecule is shown. For details see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.