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Volumn 5, Issue 16, 2003, Pages 2923-2926

Unexpected stereochemistry in the lithium salt catalyzed ring expansion of nonracemic oxaspiropentanes. Formal syntheses of (-)-(4R,5R)-muricatacin and the pheromone (R)-japonilure

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; CYCLOBUTANONE DERIVATIVE; JAPONILURE; LITHIUM DERIVATIVE; MURICATACIN; PENTANE; PHEROMONE; UNCLASSIFIED DRUG;

EID: 0141631659     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035061r     Document Type: Article
Times cited : (32)

References (51)
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    • (1970) Angew. Chem. , vol.82 , pp. 219
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    • 85037955897 scopus 로고
    • Wiechert, R. Angew. Chem. 1970, 82, 219; Angew. Chem., Int. Ed. Engl. 1970, 9, 27.
    • (1970) Angew. Chem., Int. Ed. Engl. , vol.9 , pp. 27
  • 21
    • 0001312924 scopus 로고
    • Trost, B., Fleming, I., Pattenden, G., Eds.; Pergamon Press: Oxford
    • For a complete discussion dealing with acid-catalyzed rearrangements of epoxides, see: Rickborn, B. in Comprehensive Organic Chemistry; Trost, B., Fleming, I., Pattenden, G., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p 733.
    • (1991) Comprehensive Organic Chemistry , vol.3 , pp. 733
    • Rickborn, B.1
  • 31
    • 0002561992 scopus 로고    scopus 로고
    • Nemoto, H.; Ishibashi, H.; Nagamochi, M.; Fukumoto, K. J. Org. Chem. 1992, 57, 1707. Nemoto, H.; Fukumoto, K. Synlett 1997, 863.
    • (1997) Synlett , pp. 863
    • Nemoto, H.1    Fukumoto, K.2
  • 32
    • 0001145211 scopus 로고
    • Trost, B., Fleming, I., Ley, S., Eds.; Pergamon Press: Oxford
    • Krow, G. R. In Comprehensive Organic Synthesis; Trost, B., Fleming, I., Ley, S., Eds.; Pergamon Press: Oxford, 1991; Vol. 7, p 671.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 671
    • Krow, G.R.1
  • 34
    • 0141847084 scopus 로고    scopus 로고
    • note
    • Assignment of the stereochemistry at this point of the discussion should be, of course, a tentative one, but it is justified by the evidences reported later.
  • 35
    • 0000587441 scopus 로고    scopus 로고
    • This cyclobutanone has already been prepared through a Kulinkovich reaction, but the stereochemistry is not clearly indicated. Cho, S. Y.; Cha, J. K. Org. Lett. 2000, 2, 1337.
    • (2000) Org. Lett. , vol.2 , pp. 1337
    • Cho, S.Y.1    Cha, J.K.2
  • 36
    • 0141735579 scopus 로고    scopus 로고
    • note
    • The stereogenic center of the dioxolane ring is considered to be stereochemically stable toward lithium salts.
  • 39
    • 0012816768 scopus 로고
    • Hartman, B. C.; Rickborn, B. J. Org. Chem. 1972, 37, 943. Reactions carried out in benzene and, in the case of LiBr, in the presence of HMPA. The authors report also the use of LiI as alternative to LiBr and say only that it appears to be more reactive than LiBr.
    • (1972) J. Org. Chem. , vol.37 , pp. 943
    • Hartman, B.C.1    Rickborn, B.2
  • 44
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    • Kim, K. S.; Song, Y. H.; Lee, B. H.; Hahn, C. S. J. Org. Chem. 1986, 51, 404. Fadel, A.; Yefsah, R.; Salaun, J. Synthesis 1987, 37.
    • (1987) Synthesis , pp. 37
    • Fadel, A.1    Yefsah, R.2    Salaun, J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.