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Volumn 13, Issue 11, 2011, Pages 2916-2919

Facile and enantiospecific syntheses of (6 S,7 R)-6-chloro-7-BENZYLOXY-, (7 S)-halo-, and (7 S)-hydroxy-cocaine and natural (-)-cocaine from d -(-)-ribose

Author keywords

[No Author keywords available]

Indexed keywords

COCAINE; DRUG DERIVATIVE; RIBOSE;

EID: 79957808833     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2009686     Document Type: Article
Times cited : (19)

References (33)
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    • Substance Abuse and Mental Health Services Administration. (. (Office of Applied Studies, NSDUH Series H-38A, HHS Publication No. SMA 10-4586Findings), Rockville, MD.
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    • (2010) Results from the 2009 National Survey on Drug Use and Health: Vol. I. Page 1. Summary of National Findings
  • 7
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    • For some reports of synthesis of cocaine analogues, see: racemic 6β- and 7β-methoxylated cocaine
    • For some reports of synthesis of cocaine analogues, see: racemic 6β- and 7β-methoxylated cocaine: Simoni, D.; Stoelwinder, J.; Kozikowski, A. P.; Johnson, K. M.; Bergmann, J. S.; Ball, R. G. J. Med. Chem. 1993, 36, 3975-3977
    • (1993) J. Med. Chem. , vol.36 , pp. 3975-3977
    • Simoni, D.1    Stoelwinder, J.2    Kozikowski, A.P.3    Johnson, K.M.4    Bergmann, J.S.5    Ball, R.G.6
  • 9
    • 77956574170 scopus 로고    scopus 로고
    • enantiopure C1-alkyl cocaine analogues
    • enantiopure C1-alkyl cocaine analogues: Davis, F. A.; Theddu, N.; Edupuganti, R. Org. Lett. 2010, 12, 4118-4121
    • (2010) Org. Lett. , vol.12 , pp. 4118-4121
    • Davis, F.A.1    Theddu, N.2    Edupuganti, R.3
  • 17
    • 0032511118 scopus 로고    scopus 로고
    • For previous asymmetric syntheses of cocaine, see
    • For previous asymmetric syntheses of cocaine, see: Lin, R.; Castells, J.; Rapoport, H. J. Org. Chem. 1998, 63, 4069-4078
    • (1998) J. Org. Chem. , vol.63 , pp. 4069-4078
    • Lin, R.1    Castells, J.2    Rapoport, H.3
  • 26
    • 79957813650 scopus 로고    scopus 로고
    • Our studies showed that the INAC of nitrone 22, bearing an α,β-unsaturated ester and a cis -acetonide, gave exo -cycloadduct 23 exclusively. The regio- and stereochemistry was confirmed by X-ray crystallographic analysis of its benzoate 24 (CCDC 681970).
    • Our studies showed that the INAC of nitrone 22, bearing an α,β-unsaturated ester and a cis -acetonide, gave exo -cycloadduct 23 exclusively. The regio- and stereochemistry was confirmed by X-ray crystallographic analysis of its benzoate 24 (CCDC 681970).
  • 27
    • 79957825557 scopus 로고    scopus 로고
    • Please refer to Supporting Information for X-ray structures of 9 (CCDC 737152) and 10 (CCDC 752110).
    • Please refer to Supporting Information for X-ray structures of 9 (CCDC 737152) and 10 (CCDC 752110).
  • 28
    • 79957814104 scopus 로고    scopus 로고
    • The structure of azetidine-diol 12 was confirmed by X-ray crystallographic analysis of its tribenzoate derivative (CCDC 798275). Its preparation is described in the Supporting Information.
    • The structure of azetidine-diol 12 was confirmed by X-ray crystallographic analysis of its tribenzoate derivative (CCDC 798275). Its preparation is described in the Supporting Information.
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    • The existence of such ammonium ion 18 was supported by the racemization of acetate product upon acetylation of l -2 α -tropanol as reported by Archer et al.; see
    • The existence of such ammonium ion 18 was supported by the racemization of acetate product upon acetylation of l -2 α -tropanol as reported by Archer et al.; see: Archer, S.; Lewis, T. R.; Bell, M. R.; Schulenberg, J. W. J. Am. Chem. Soc. 1961, 83, 2386-2387
    • (1961) J. Am. Chem. Soc. , vol.83 , pp. 2386-2387
    • Archer, S.1    Lewis, T.R.2    Bell, M.R.3    Schulenberg, J.W.4
  • 31
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    • The (7 R)-hydroxy cocaine had been used to synthesize haptens for immunopharmacotherapy in cocaine abuse; see
    • The (7 R)-hydroxy cocaine had been used to synthesize haptens for immunopharmacotherapy in cocaine abuse; see: Ino, A.; Dickerson, T. J.; Janda, K. D. Bioorg. Med. Chem. Lett. 2007, 17, 4280-4283
    • (2007) Bioorg. Med. Chem. Lett. , vol.17 , pp. 4280-4283
    • Ino, A.1    Dickerson, T.J.2    Janda, K.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.