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Volumn 39, Issue 27, 1998, Pages 4789-4792

Formal synthesis of natural epibatidine and of its enantiomer: Use of radical cyclization in an enantiospecific route

Author keywords

[No Author keywords available]

Indexed keywords

(PHENYLTHIO)ACETYLENE; 7 AZABICYCLO[2.2.1]HEPTANE; ACETYLENE DERIVATIVE; EPIBATIDINE; HEPTANE; PYROGLUTAMIC ACID; UNCLASSIFIED DRUG;

EID: 0032474789     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00958-7     Document Type: Article
Times cited : (40)

References (55)
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    • 7 Reviews: Chen, Z.; Trudell, M. L. Chem. Rev. 1996, 96, 1179-1193. Broka, C. A. Med. Chem. Res. 1994, 4, 449-460. Szántay, C.; Kardos-Balogh, Z.; Szántay, C., Jr. The Alkaloids; Academic Press: New York, 1995; Vol. 46, p 95-125.
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    • 13 Hardegger, E.; Ott, H. Helv. Chim. Acta 1955, 38, 312-315. Cf. Drauz, K.; Kleemann, A.; Martens, J.; Scherberich, P.; Effenberger, F. J. Org. Chem. 1986, 51, 3494-3498.
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    • and were prepared along the same lines; we used the methyl esters simply as a matter of convenience
    • 15 The ethyl esters corresponding to 8 have been reported (Dieter, R. K.; Sharma, R. R. J. Org. Chem. 1996, 61, 4180-4184), and were prepared along the same lines; we used the methyl esters simply as a matter of convenience.
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    • for deoxygenation, but this procedure was not successful
    • 2Ph, R′ = OMe or SPh; R″ = CHO) a palladium-based method (Cf. Mandai, T.; Matsumoto, T.; Tsujiguchi, Y.; Matsuoka, S.; Tsuji, J. J. Organomet. Chem. 1994, 474, 343-352) for deoxygenation, but this procedure was not successful. We did not try the case for R = Ms (Cf. Whitlock, G. A.; Carreira, E. M. J. Org. Chem. 1997, 62, 7916-7917).
    • (1994) J. Organomet. Chem. , vol.474 , pp. 343-352
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    • (1997) J. Org. Chem. , vol.62 , pp. 7916-7917
    • Whitlock, G.A.1    Carreira, E.M.2
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    • note
    • (Equation Presented)
  • 53
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    • 20 For early studies on radical cyclization of 2-(phenylthio)pyrrolidones, see, for example: Dener, J. M.; Hart, D J.; Ramesh, S. J. Org. Chem. 1988, 53, 6022-6030.
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    • Dener, J.M.1    Hart, D.J.2    Ramesh, S.3
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    • note
    • 3) (reference 11f).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.