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Volumn 8, Issue 25, 2006, Pages 5805-5808

Two convergent routes to the left-wing fragment of ciguatoxin CTX3C using O,S-acetals as key intermediates

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALKENE; CIGUATOXIN; CIGUATOXIN 3C; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; UNCLASSIFIED DRUG;

EID: 33846316751     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol062350h     Document Type: Article
Times cited : (38)

References (56)
  • 4
  • 15
    • 0035832058 scopus 로고    scopus 로고
    • For syntheses of the BCDE, ABCD, or ABCDE ring part of ciguatoxins from other groups, see: a
    • For syntheses of the BCDE, ABCD, or ABCDE ring part of ciguatoxins from other groups, see: (a) Kira, K.; Isobe, M. Tetrahedron Lett. 2001, 42, 2821.
    • (2001) Tetrahedron Lett , vol.42 , pp. 2821
    • Kira, K.1    Isobe, M.2
  • 23
    • 0034246704 scopus 로고    scopus 로고
    • (c) Yet, L. Chem. Rev. 2000, 100, 2963.
    • (2000) Chem. Rev , vol.100 , pp. 2963
    • Yet, L.1
  • 25
    • 30744459350 scopus 로고    scopus 로고
    • (e) Nakata, T. Chem. Rev. 2005, 105, 4314.
    • (2005) Chem. Rev , vol.105 , pp. 4314
    • Nakata, T.1
  • 26
    • 30744476469 scopus 로고    scopus 로고
    • (f) Inoue, M. Chem. Rev. 2005, 105, 4379.
    • (2005) Chem. Rev , vol.105 , pp. 4379
    • Inoue, M.1
  • 28
    • 0039377396 scopus 로고    scopus 로고
    • For reviews on acyl radicals, see: a
    • For reviews on acyl radicals, see: (a) Boger, D. L. Isr. J. Chem. 1997, 37, 119.
    • (1997) Isr. J. Chem , vol.37 , pp. 119
    • Boger, D.L.1
  • 36
    • 33846331389 scopus 로고    scopus 로고
    • Compounds 4a-c were synthesized by standard functional group transformation from the previously reported E-ring fragment (ref 6a).
    • Compounds 4a-c were synthesized by standard functional group transformation from the previously reported E-ring fragment (ref 6a).
  • 39
    • 0030061008 scopus 로고    scopus 로고
    • Related tandem radical cyclizations were reported by Pattenden. (a) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
    • Related tandem radical cyclizations were reported by Pattenden. (a) Hayes, C. J.; Pattenden, G. Tetrahedron Lett. 1996, 37, 271.
  • 42
    • 0029976190 scopus 로고    scopus 로고
    • Evans successfully applied these reaction conditions to construction of the five-, six-, and seven-membered ether rings through acyl radical addition to vinylogous carbonates and sulfonates: (a) Evans, P. A.; Roseman, J. D. J. Org. Chem. 1996, 61, 2252.
    • Evans successfully applied these reaction conditions to construction of the five-, six-, and seven-membered ether rings through acyl radical addition to vinylogous carbonates and sulfonates: (a) Evans, P. A.; Roseman, J. D. J. Org. Chem. 1996, 61, 2252.
  • 47
    • 33846309386 scopus 로고    scopus 로고
    • The increased ratio of the trans-isomer of aldehyde 21 (cis:trans, 1:11) implied the more efficient cyclization of the cis-isomer of 16c. For the discussion on cyclization efficiency of the geometric isomers, see ref 8
    • The increased ratio of the trans-isomer of aldehyde 21 (cis:trans = 1:11) implied the more efficient cyclization of the cis-isomer of 16c. For the discussion on cyclization efficiency of the geometric isomers, see ref 8.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.