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Volumn 55, Issue 12, 1999, Pages 3791-3802

New radical reactions of S-alkoxycarbonyl xanthates. Total synthesis of (±)-cinnamolide and (±)-methylenolactocin

Author keywords

Lactones; Radical reactions; Terpenes; Xanthates

Indexed keywords

CARBON DIOXIDE; CINNAMOLIDE; LACTONE; METHYLENOLACTOCIN; UNCLASSIFIED DRUG; XANTHIC ACID DERIVATIVE;

EID: 0033583016     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01184-3     Document Type: Article
Times cited : (42)

References (52)
  • 2
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    • Editors: B. Trost and I. Fleming, Pergamon Press
    • b) Curran, D. P. In: Comprehensive Organic Synthesis, Editors: B. Trost and I. Fleming, Pergamon Press, 1991, Vol. 4, p. 715-831.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 715-831
    • Curran, D.P.1
  • 8
    • 0001329885 scopus 로고
    • and references cited therein
    • (a) Bachi, M. D.; Bosch, E.J. Org. Chem. 1992,57, 4696-4705 and references cited therein.
    • (1992) J. Org. Chem. , vol.57 , pp. 4696-4705
    • Bachi, M.D.1    Bosch, E.2
  • 11
    • 0025277178 scopus 로고
    • For preliminary communications on this subject see: (b) Forbes, J. E.; Zard, S. Z. J. Am. Chem. Soc. 1990, 112, 2034-2035.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 2034-2035
    • Forbes, J.E.1    Zard, S.Z.2
  • 22
    • 0027479919 scopus 로고
    • Recently a modification of the Barton-McCombie reaction allowing for deoxygenation of primary alcohols at low temperatures was reported: Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. C. S. Tetrahedron 1993, 49, 2793-2796.
    • (1993) Tetrahedron , vol.49 , pp. 2793-2796
    • Barton, D.H.R.1    Jang, D.O.2    Jaszberenyi, J.C.S.3
  • 23
  • 46
    • 0001091186 scopus 로고
    • Editors: B. Trost and I. Fleming, Pergamon Press
    • In principle, the starting homoallylic alcohol a can be made in optically pure form through the now well established asymmetric aldol technology: Moon Kirn, B.; Williams, S. F. and Masamune, S., In: Comprehensive Organic Synthesis, Editors: B. Trost and I. Fleming, Pergamon Press, 1991, Vol. 2, p. 239-275.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 239-275
    • Moon Kirn, B.1    Williams, S.F.2    Masamune, S.3
  • 51
    • 0013628631 scopus 로고    scopus 로고
    • note
    • Inverse order of addition leads to the decomposition of S-alkoxycarbonyl xanthate. For the mechanism of this anionic chain reaction see ref. (4a).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.