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Volumn 2, Issue 18, 2000, Pages 2917-2919

Synthesis of oxepanes and trans-fused bisoxepanes via biomimetic, endo-regioselective tandem oxacyclizations of polyepoxides

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; MARINE TOXIN; OXEPINE DERIVATIVE; POLYCYCLIC HYDROCARBON;

EID: 0034618330     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0064009     Document Type: Article
Times cited : (69)

References (46)
  • 11
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    • (a) Previously reported tandem endo-oxacyclizations have been limited to low-yield formation of three six-membered rings from a 1,4,7-triepoxide: Tokiwano, T.; Fujiwara, K.; Murai, A. Synlett 2000, 335.
    • (2000) Synlett , pp. 335
    • Tokiwano, T.1    Fujiwara, K.2    Murai, A.3
  • 12
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    • (b) An earlier approach from a 1,4-diepoxide proceeded via an unexpected double inversion to afford the cis-fused bispyran: Hayashi, N.; Fujiwara, K.; Murai, A. Tetrahedron Lett. 1996, 37, 6173.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 6173
    • Hayashi, N.1    Fujiwara, K.2    Murai, A.3
  • 13
    • 0028913329 scopus 로고
    • endo-Regioselectivity in monooxacyclizations has been observed with antibody (ref 5a) or Co-salen catalysis (ref 5b), or more generally by placing cation-stabilizing or other directing substituents onto the epoxide (ref 5c -k). (a) Janda, K. D.; Shevlin, C. G.; Lerner, R. A. J. Am. Chem. Soc. 1995, 117, 2659.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 2659
    • Janda, K.D.1    Shevlin, C.G.2    Lerner, R.A.3
  • 24
    • 0032532258 scopus 로고    scopus 로고
    • Review of oxepane synthesis
    • (l) Review of oxepane synthesis: Hoberg, J. O. Tetrahedron 1998, 54, 12631.
    • (1998) Tetrahedron , vol.54 , pp. 12631
    • Hoberg, J.O.1
  • 25
    • 0000406679 scopus 로고
    • Other examples in which epoxides have been utilized as nucleophiles in oxacyclization transformations include ref 4b and (a) David, F. J. Org. Chem. 1981, 46, 3512.
    • (1981) J. Org. Chem. , vol.46 , pp. 3512
    • David, F.1
  • 31
    • 18844410382 scopus 로고
    • Shi epoxidation of the 6,7-alkene, and acetylation of the primary alcohol
    • Prepared from geraniol by a sequence of Sharpless enantioselective epoxidation of the 2,3-alkene (Gao, Y.; Klunder, J. M.; Hanson, R. M.; Masamune, H.; Ko, S. Y.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765), Shi epoxidation of the 6,7-alkene, and acetylation of the primary alcohol.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 5765
    • Gao, Y.1    Klunder, J.M.2    Hanson, R.M.3    Masamune, H.4    Ko, S.Y.5    Sharpless, K.B.6
  • 32
    • 85088004423 scopus 로고    scopus 로고
    • note
    • 2 = 0.1129, GoF 1.168.
  • 33
    • 0002839259 scopus 로고
    • via sequential Sharpless enantioselective epoxidation of the 2-methylene and Shi epoxidation of the remaining 5,6-alkene followed by acetylation of the primary alcohol
    • Prepared from 6-methyl-2-methylene-hept-5-en-1-ol (Takano, S.; Morimoto, M.; Satoh, S.; Ogasawara, K. Chem. Lett. 1984, 1261) via sequential Sharpless enantioselective epoxidation of the 2-methylene and Shi epoxidation of the remaining 5,6-alkene followed by acetylation of the primary alcohol.
    • (1984) Chem. Lett. , pp. 1261
    • Takano, S.1    Morimoto, M.2    Satoh, S.3    Ogasawara, K.4
  • 34
    • 85088005450 scopus 로고    scopus 로고
    • note
    • 2 = 0.0929, GoF 1.123.
  • 35
    • 0039155654 scopus 로고    scopus 로고
    • note
    • We have not excluded the possibility of a concerted oxacyclization process rather than the stepwise mechanism shown in Figure 2.
  • 36
    • 0040934096 scopus 로고    scopus 로고
    • note
    • Prepared from E,E-farnesol by a three-step sequence of Sharpless enantioselective epoxidation of the 2,3-alkene, Shi epoxidation of the remaining 6,7- and 10,11-alkenes, and tert-butyl carbonate derivatization of the primary alcohol.
  • 38
    • 0033534422 scopus 로고    scopus 로고
    • (b) Koohang, A.; Coates, R. M.; Owen, D.; Poulter, C. D. J. Org. Chem. 1999, 64, 6.] via sequential Sharpless enantioselective epoxidation of the 2-methylene, Shi epoxidation of the remaining 5,6- and 9,10-alkenes, and tert-butyl carbonate derivatization of the primary hydroxyl.
    • (1999) J. Org. Chem. , vol.64 , pp. 6
    • Koohang, A.1    Coates, R.M.2    Owen, D.3    Poulter, C.D.4
  • 39
    • 85088003768 scopus 로고    scopus 로고
    • note
    • 2 = 0.0575, GoF 1.082.
  • 40
    • 0001418150 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: New York
    • Reviews: (a) Bartlett, P. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, pp 341-409.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 341-409
    • Bartlett, P.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.