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Volumn 122, Issue 38, 2000, Pages 9127-9133

Nondynamic and dynamic kinetic resolution of lactones with stereogenic centers and axes: Stereoselective total synthesis of herbertenediol and mastigophorenes A and B

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; DIMER; HALOGEN; HERBERTENEDIOL; LACTONE DERIVATIVE; MASTIGOPHORENE A; MASTIGOPHORENE B; OXAZABOROLIDINE DERIVATIVE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0034721428     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja001455r     Document Type: Article
Times cited : (87)

References (40)
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    • Strictly speaking such "dimers" should be described as "dehydrodimers"
    • Strictly speaking such "dimers" should be described as "dehydrodimers".
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    • The elimination step to ethyl 1,2-dimethyl-cyclopent-2-enoate was done by azeotropic removal of water with toluene and p-toluenesulfonic acid. Subsequent hydrolysis as described gave (rac)-8 in 72% yield (2 steps)
    • Klärner, F.-G.; Adamsky, F. Chem. Ber. 1983, 116, 299. The elimination step to ethyl 1,2-dimethyl-cyclopent-2-enoate was done by azeotropic removal of water with toluene and p-toluenesulfonic acid. Subsequent hydrolysis as described gave (rac)-8 in 72% yield (2 steps).
    • (1983) Chem. Ber. , vol.116 , pp. 299
    • Klärner, F.-G.1    Adamsky, F.2
  • 21
    • 0000750794 scopus 로고    scopus 로고
    • Schreier, P., Herderich, M., Humpf, H.-U., Schwab, W., Eds.; Vieweg: Braunschweig
    • Bringmann, G.; Busemann, S. In Natural Product Analysis; Schreier, P., Herderich, M., Humpf, H.-U., Schwab, W., Eds.; Vieweg: Braunschweig, 1998; pp 195-212.
    • (1998) Natural Product Analysis , pp. 195-212
    • Bringmann, G.1    Busemann, S.2
  • 23
    • 0001207373 scopus 로고
    • For the synthesis of related - albeit sterically less hindered-biaryl lactones by other methods, see: (a) Wang, W.; Snieckus, V. J. Org. Chem. 1992, 57, 424. (b) Davies, D. I.; Waring, C. J. Chem. Soc. C 1967, 1639 and references cited therein. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37, 8953.
    • (1992) Org. Chem. , vol.57 , pp. 424
    • Wang, W.1    Snieckus, V.J.2
  • 24
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    • and references cited therein
    • For the synthesis of related - albeit sterically less hindered-biaryl lactones by other methods, see: (a) Wang, W.; Snieckus, V. J. Org. Chem. 1992, 57, 424. (b) Davies, D. I.; Waring, C. J. Chem. Soc. C 1967, 1639 and references cited therein. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37, 8953.
    • (1967) J. Chem. Soc. C , pp. 1639
    • Davies, D.I.1    Waring, C.2
  • 25
    • 0030566846 scopus 로고    scopus 로고
    • For the synthesis of related - albeit sterically less hindered-biaryl lactones by other methods, see: (a) Wang, W.; Snieckus, V. J. Org. Chem. 1992, 57, 424. (b) Davies, D. I.; Waring, C. J. Chem. Soc. C 1967, 1639 and references cited therein. de Frutos, O.; Echavarren, A. M. Tetrahedron Lett. 1996, 37, 8953.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 8953
    • De Frutos, O.1    Echavarren, A.M.2
  • 32
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    • (c) Dyker, G. Chem. Ber. 1994, 127, 7, 739.
    • (1994) Chem. Ber. , vol.127 , Issue.7 , pp. 739
    • Dyker, G.1
  • 33
    • 0343602747 scopus 로고    scopus 로고
    • note
    • -1.
  • 37
    • 0343602746 scopus 로고    scopus 로고
    • note
    • (31 ) This reaction sequence was first optimized with a simplified model system, bearing a tert-bulyl group instead of the chiral cyclopentyl residue; for the characterization of these compounds see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.