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Volumn 48, Issue 12, 2007, Pages 2171-2175

Convergent synthesis of the ABCDE-ring fragment of the Caribbean ciguatoxin C-CTX-1

Author keywords

Ciguatoxins; Enol ethers; O,S Acetals; Polyethers; Radicals

Indexed keywords

CIGUATOXIN; TOXIN;

EID: 33847023052     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.01.102     Document Type: Article
Times cited : (13)

References (68)
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    • For syntheses of the BCDE, ABCD or ABCDE ring units of the Pacific ciguatoxins from other groups, see:
    • For syntheses of the BCDE, ABCD or ABCDE ring units of the Pacific ciguatoxins from other groups, see:. Kira K., and Isobe M. Tetrahedron Lett. 42 (2001) 2821
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    • 2-promoted reaction could be different from that of the proton-catalyzed reaction. Ha proposed that the rhodium catalyst induced the formation of an enyl or a π-allyl intermediate prior to the cyclization. For similar reactions, see:
    • 2-promoted reaction could be different from that of the proton-catalyzed reaction. Ha proposed that the rhodium catalyst induced the formation of an enyl or a π-allyl intermediate prior to the cyclization. For similar reactions, see:. Fagnou K., and Lautens M. Org. Lett. 2 (2000) 2319
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    • Compounds 8 were synthesized by standard functional group transformation from the previously reported E-ring fragment of CTX3C.
    • Compounds 8 were synthesized by standard functional group transformation from the previously reported E-ring fragment of CTX3C. Maruyama M., Inoue M., Oishi T., Oguri H., Ogasawara Y., Shindo Y., and Hirama M. Tetrahedron 58 (2002) 1835
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    • note
    • The geometric isomer ratio of 5 did not reflect the diastereomer ratio at the O,S-acetal carbon center of 6, indicating an E1-like mechanism of the reaction.
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    • Evans successfully constructed the seven-membered ether rings through acyl radical addition to electron deficient olefins such as vinyl esters and sulfonates:
    • Evans successfully constructed the seven-membered ether rings through acyl radical addition to electron deficient olefins such as vinyl esters and sulfonates:. Evans P.A., and Roseman J.D. J. Org. Chem. 61 (1996) 2252
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    • note
    • +), found 597.2821.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.