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Volumn 130, Issue 41, 2008, Pages 13765-13770

Total syntheses of (+)- and (-)-peribysin E

Author keywords

[No Author keywords available]

Indexed keywords

CELL ADHESION; CHEMICAL REACTIONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 53849102606     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8048207     Document Type: Article
Times cited : (67)

References (38)
  • 3
    • 33744493376 scopus 로고    scopus 로고
    • (b) Baselga, J. Science 2006, 312, 1175-1178.
    • (2006) Science , vol.312 , pp. 1175-1178
    • Baselga, J.1
  • 7
    • 53849104478 scopus 로고    scopus 로고
    • The structure including absolute as well as relative stereochemistry was assigned as shown in structure 1
    • The structure including absolute as well as relative stereochemistry was assigned as shown in structure 1.
  • 20
    • 0000311991 scopus 로고    scopus 로고
    • For related transformations in the AB trans series, see: (a) Paquette, L. A.; Wang, T.-Z.; Philippo, C. M. G.; Wang, S. J. Am. Chem. Soc. 1994, 116, 3367-3374.
    • For related transformations in the AB trans series, see: (a) Paquette, L. A.; Wang, T.-Z.; Philippo, C. M. G.; Wang, S. J. Am. Chem. Soc. 1994, 116, 3367-3374.
  • 26
    • 33845282582 scopus 로고    scopus 로고
    • The very high level of stereoselection in the nucleophilic epoxidation presumably reflects the mutually compatible tendencies for attack by the hydroperoxide anion from the convex face along an axial trajectory cf. Wu, Y-D, Houk, K. N, Trost, B. M. J. Am. Chem. Soc. 1987, 109, 5560-5561, The presence of cis-1,3-related substituents in the B-ring of 31 may well serve to anchor the conformation of the system such that attack from the β-face corresponds to axial attack
    • (b) The very high level of stereoselection in the nucleophilic epoxidation presumably reflects the mutually compatible tendencies for attack by the hydroperoxide anion from the convex face along an axial trajectory (cf. Wu, Y-D.; Houk, K. N.; Trost, B. M. J. Am. Chem. Soc. 1987, 109, 5560-5561). The presence of cis-1,3-related substituents in the B-ring of 31 may well serve to anchor the conformation of the system such that attack from the β-face corresponds to axial attack.
  • 27
    • 53849138541 scopus 로고    scopus 로고
    • The relative stereochemistry of 33 was established by crystallographic determination on a derived triol (Supporting Information).
    • The relative stereochemistry of 33 was established by crystallographic determination on a derived triol (Supporting Information).
  • 29
    • 0003417469 scopus 로고
    • Trost, B. M, Fleming, I, Ed, Pergamon: Oxford
    • Gill, G. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ed.; Pergamon: Oxford, 1991; pp 821-838.
    • (1991) Comprehensive Organic Synthesis , pp. 821-838
    • Gill, G.B.1
  • 31
    • 0343517256 scopus 로고    scopus 로고
    • Experimentally determined deuterium isotope effects for 1,2-hydride shifts lie in the range of 1.2-3.0: (a) Myhre, P. C.; Brown, K. S. J. Am. Chem. Soc. 1969, 91, 5639-5641.
    • Experimentally determined deuterium isotope effects for 1,2-hydride shifts lie in the range of 1.2-3.0: (a) Myhre, P. C.; Brown, K. S. J. Am. Chem. Soc. 1969, 91, 5639-5641.
  • 38
    • 0345255697 scopus 로고    scopus 로고
    • M, E.; Jung, A.; van den Heuvel, A. G.; Leach, K. N.; Houk, Org. Lett. 2003, 5, 3375-3378.
    • M, E.; Jung, A.; van den Heuvel, A. G.; Leach, K. N.; Houk, Org. Lett. 2003, 5, 3375-3378.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.