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Volumn 37, Issue 7, 1998, Pages 965-969

Synthetic studies on ciguatoxin: A convergent strategy for construction of the F-M ring framework

Author keywords

Ciguatoxin; Cyclizations; Natural products; Polyethers; Synthetic methods

Indexed keywords


EID: 0031980536     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980420)37:7<965::AID-ANIE965>3.0.CO;2-P     Document Type: Article
Times cited : (51)

References (48)
  • 10
    • 0031550831 scopus 로고    scopus 로고
    • The absolute stereochemistry of ciguatoxin was determined to be that represented by structure 1; see a) H. Oguri, S. Hishiyama, O. Sato, T. Oishi, M. Hirama, M. Murata, T. Yasumoto, N. Harada, Tetrahedron 1997, 53, 3057-3072; b) M. Satake, A. Morohashi, H. Oguri, T. Oishi, M. Hirama, N. Harada, T. Yasumoto, J. Am. Chem. Soc. 1997, 119, 11325-11326.
    • (1997) Tetrahedron , vol.53 , pp. 3057-3072
    • Oguri, H.1    Hishiyama, S.2    Sato, O.3    Oishi, T.4    Hirama, M.5    Murata, M.6    Yasumoto, T.7    Harada, N.8
  • 11
    • 0030670907 scopus 로고    scopus 로고
    • The absolute stereochemistry of ciguatoxin was determined to be that represented by structure 1; see a) H. Oguri, S. Hishiyama, O. Sato, T. Oishi, M. Hirama, M. Murata, T. Yasumoto, N. Harada, Tetrahedron 1997, 53, 3057-3072; b) M. Satake, A. Morohashi, H. Oguri, T. Oishi, M. Hirama, N. Harada, T. Yasumoto, J. Am. Chem. Soc. 1997, 119, 11325-11326.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 11325-11326
    • Satake, M.1    Morohashi, A.2    Oguri, H.3    Oishi, T.4    Hirama, M.5    Harada, N.6    Yasumoto, T.7
  • 30
    • 0030944753 scopus 로고    scopus 로고
    • Recent reviews: a) E. Alvarez, M.-L. Candenas, R. Pérez, J. L. Ravelo, J. D. Martín, Chem. Rev. 1995, 95, 1953-1980; b) Y. Mori, Chem. Eur. J. 1997, 3, 849-852.
    • (1997) Chem. Eur. J. , vol.3 , pp. 849-852
    • Mori, Y.1
  • 32
    • 0344623904 scopus 로고    scopus 로고
    • note
    • The numbering of carbon atoms in all compounds in this communication corresponds to that of ciguatoxin.
  • 39
    • 0345054434 scopus 로고    scopus 로고
    • note
    • Use of 10-camphorsulfonic acid as an acid catalyst in this acetalization gave a 1:1 mixture of acetals 10.
  • 40
    • 0344623902 scopus 로고    scopus 로고
    • note
    • When chlorotrimethylsilane was used as silylating agent, a significant amount (10-20% yield) of α-alkoxyallylsilane was formed as a byproduct.
  • 42
    • 0345054436 scopus 로고    scopus 로고
    • note
    • From the corresponding γ-alkoxyallyltrimethylsilane, cyclization of the β-H isomer gave the desired (23S,24A)-5 in 42% yield as the major product together with its (23R,24R) diastereoisomer (30%), whereas cyclization of the α-H isomer produced 5 in only 29% yield together with three other stereoisomers for C23 and C24 in yields of 28, 27, and 13%.
  • 43
    • 0345486074 scopus 로고    scopus 로고
    • note
    • The configuration at C27 of 14 was assigned on the basis of strong NOEs between 24-H/27-H and 27-H/29-H. The syn relationship between 23-H and 30-H was also confirmed by NOE experiments.
  • 44
    • 0345054437 scopus 로고    scopus 로고
    • note
    • β-Acetoxy ketone 14 underwent partial β-elimination during chromatography over silica gel to yield the α,β-unsaturated ketone.
  • 46
    • 0344192186 scopus 로고    scopus 로고
    • note
    • The syn relationship between 36-H and 42-H in compound 21 was unambiguously established by NOE experiments.
  • 48
    • 0345486073 scopus 로고    scopus 로고
    • note
    • +]: 783.4295, found: 783.4285.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.