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Volumn 125, Issue 39, 2003, Pages 11893-11899

Convergent total syntheses of gambierol and 16-epi-gambierol and their biological activities

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL MODIFICATION; ETHERS; TOXICITY;

EID: 0141508988     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja036984k     Document Type: Article
Times cited : (103)

References (60)
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    • For reviews on marine polycyclic ethers, see: (a) Shimizu, Y. Chem. Rev. 1993, 93, 1685-1698.
    • (1993) Chem. Rev. , vol.93 , pp. 1685-1698
    • Shimizu, Y.1
  • 10
    • 0001399218 scopus 로고    scopus 로고
    • Also see: (e) Hoberg, J. O. Tetrahedron 1998, 54, 12630-12670.
    • (1998) Tetrahedron , vol.54 , pp. 12630-12670
    • Hoberg, J.O.1
  • 51
    • 0141747329 scopus 로고    scopus 로고
    • note
    • Sasaki found an effective catalyst system for the coupling of Z-bromo-alkenes, see ref 5.
  • 52
    • 0141747328 scopus 로고    scopus 로고
    • note
    • 3SnH was not selective, see ref 19c.
  • 53
    • 0141524205 scopus 로고    scopus 로고
    • note
    • The iodoolefination of the corresponding aldehyde using Wittig reagent gave a mixture of stereoisomers.
  • 56
    • 0038648266 scopus 로고    scopus 로고
    • Very recently, Sasaki reported the biological evaluation of synthetic gambierol analogues varied with the H ring functionalities, see: Fuwa, H.; Kainuma, N.; Satake, M.; Sasaki, M. Bioorg. Med. Chem. Lett. 2003, 13, 2519-2522.
    • (2003) Bioorg. Med. Chem. Lett. , vol.13 , pp. 2519-2522
    • Fuwa, H.1    Kainuma, N.2    Satake, M.3    Sasaki, M.4
  • 57
    • 0001408299 scopus 로고
    • For a example of the use of amines as a catalyst poison, see: Czech, B. P.; Bartsch, R. A. J. Org. Chem. 1984, 49, 4076-4078.
    • (1984) J. Org. Chem. , vol.49 , pp. 4076-4078
    • Czech, B.P.1    Bartsch, R.A.2
  • 59
    • 0141524199 scopus 로고    scopus 로고
    • note
    • 2/MeOH = 20:1) indicated the significant difference of their polarity. See Supporting Information.
  • 60
    • 0037376955 scopus 로고    scopus 로고
    • Recently, inhibition of brevetoxin binding to the voltage-gated sodium channel by natural gambierol was reported, see: Inoue, M.; Hirama, M.; Satake, M.; Suguyama, K.; Yasumoto, T. Toxicon 2003, 41, 469-474.
    • (2003) Toxicon , vol.41 , pp. 469-474
    • Inoue, M.1    Hirama, M.2    Satake, M.3    Suguyama, K.4    Yasumoto, T.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.