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Volumn 68, Issue 15, 2003, Pages 5917-5924

The rearrangement of 2,3-epoxysulfonates and its application to natural products syntheses: Formal synthesis of (-)-aphanorphine and total syntheses of (-)-α-herbertenol and (-)-herbertenediol

Author keywords

[No Author keywords available]

Indexed keywords

NATURAL PRODUCTS;

EID: 0038373088     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034573g     Document Type: Article
Times cited : (75)

References (52)
  • 7
    • 0034719737 scopus 로고    scopus 로고
    • (b) Kita, Y.; Furukawa, A.; Futamura, J.; Higuchi, K.; Ueda, K.; Fujioka, H. Tetrahedron Lett. 2000, 41, 2133-2136. Quite recently we found that the reaction of acyclic 2-aryl-2,3-epoxy acylates proceeded via the C3-cleavage of the oxirane ring. However, the intermediates are phenonium ions, which are completely different from the intermediates of eqs 1 and 2 due to the flexibility of the substrates. Kita, Y.; Furukawa, A.; Futamura, J.; Higuchi, K.; Ueda, K.; Fujioka, H. Tetrahedron 2001, 57, 815-825.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 2133-2136
    • Kita, Y.1    Furukawa, A.2    Futamura, J.3    Higuchi, K.4    Ueda, K.5    Fujioka, H.6
  • 8
    • 0035961113 scopus 로고    scopus 로고
    • (b) Kita, Y.; Furukawa, A.; Futamura, J.; Higuchi, K.; Ueda, K.; Fujioka, H. Tetrahedron Lett. 2000, 41, 2133-2136. Quite recently we found that the reaction of acyclic 2-aryl-2,3-epoxy acylates proceeded via the C3-cleavage of the oxirane ring. However, the intermediates are phenonium ions, which are completely different from the intermediates of eqs 1 and 2 due to the flexibility of the substrates. Kita, Y.; Furukawa, A.; Futamura, J.; Higuchi, K.; Ueda, K.; Fujioka, H. Tetrahedron 2001, 57, 815-825.
    • (2001) Tetrahedron , vol.57 , pp. 815-825
    • Kita, Y.1    Furukawa, A.2    Futamura, J.3    Higuchi, K.4    Ueda, K.5    Fujioka, H.6
  • 10
    • 0038271016 scopus 로고    scopus 로고
    • note
    • In this section, racemic epoxysulfonates were used to examine their reactivity under Lewis acid treatment.
  • 11
    • 0038271017 scopus 로고    scopus 로고
    • note
    • The reaction mechanism for compounds 3 and 4 will be discussed elsewhere.
  • 26
    • 33845282438 scopus 로고
    • Corey, E. J.; Bakshi, R. K.; Shibata. S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. Soc. 1987, 109, 7925-7926. The absolute configuration of the secondary alcohol was deduced by referring to the literature and our previous study (refs 1-3). This deduction was consequently determined by agreement of the synthesized 10 to the authentic one.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 7925-7926
    • Corey, E.J.1    Bakshi, R.K.2    Shibata, S.3    Chen, C.-P.4    Singh, V.K.5
  • 33
    • 0037933610 scopus 로고    scopus 로고
    • note
    • For racemic synthesis, see ref 21f and references therein.
  • 49
    • 0035961113 scopus 로고    scopus 로고
    • The same tendency in the formation of the phenonium ion intermediate, i.e., the difference between the cyclic system not forming the phenonium ion and the acyclic system forming the phenonium ion, was observed in our previous study; see: Kita, Y.; Furukawa, A.; Futamura, J.; Higuchi, K.; Ueda, K.; Fujioka, H. Tetrahedron 2001, 57, 815-825.
    • (2001) Tetrahedron , vol.57 , pp. 815-825
    • Kita, Y.1    Furukawa, A.2    Futamura, J.3    Higuchi, K.4    Ueda, K.5    Fujioka, H.6
  • 50
    • 33947087514 scopus 로고
    • Burgess, E. M.; Penton, H. R., Jr.; Taylor, E. A. J. Org. Chem. 1973, 38, 26-31. For a successful result, see: Kita, Y.; Higuchi, K.; Yoshida, Y.; Iio, K.; Kitagaki, S.; Ueda, K.; Akai, S.; Fujioka, H. J. Am. Chem. Soc. 2001, 123, 3214-3222.
    • (1973) J. Org. Chem. , vol.38 , pp. 26-31
    • Burgess, E.M.1    Penton H.R., Jr.2    Taylor, E.A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.