Synthesis of the EF-Ring of Ciguatoxin 3C Based on the [2,3]-Wittig Rearrangement and Ring-Closing Olefin Metathesis
作者： Akiyoshi Goto , Kenshu Fujiwara , Ayako Kawai , Hidetoshi Kawai , Takanori Suzuki
DOI: 10.1021/OL702231J
关键词: Ciguatoxin 3C 、 2,3-Wittig rearrangement 、 Ciguatera fish poisoning 、 Ring (chemistry) 、 Stereochemistry 、 Ether 、 Olefin metathesis 、 Chemistry 、 Chirality (chemistry)
摘要: The EF-ring segment of ciguatoxin 3C, a causative toxin ciguatera fish poisoning, was synthesized in three major steps: 1,4-addition for the C20O−C27 bond connection, chirality transferring anti selective [2,3]-Wittig rearrangement construction anti-2-hydroxyalkyl ether part, and ring-closing olefin metathesis F-ring formation.
acs.org
sci-hub.se 参考文章(32)
Yoshitsugi Hokama, Warren E Takenaka, Kristi L Nishimura, Joanne S M Ebesu, Robert Bourke, Patrick K Sullivan, A simple membrane immunobead assay for detecting ciguatoxin and related polyethers from human ciguatera intoxication and natural reef fishes. Journal of AOAC International. ,vol. 81, pp. 727- 735 ,(1998) , 10.1093/JAOAC/81.4.727
R J Auchus, D F Covey, V Bork, J Schaefer, Solid-state NMR observation of cysteine and lysine Michael adducts of inactivated estradiol dehydrogenase. Journal of Biological Chemistry. ,vol. 263, pp. 11640- 11645 ,(1988) , 10.1016/S0021-9258(18)37832-3
Masahiro Hirama, Tohru Oishi, Hisatoshi Uehara, Masayuki Inoue, Megumi Maruyama, Hiroki Oguri, Masayuki Satake, Total Synthesis of Ciguatoxin CTX3C Science. ,vol. 294, pp. 1904- 1907 ,(2001) , 10.1126/SCIENCE.1065757
Alessandro Dondoni, Giancarlo Fantin, Marco Fogagnolo, Alessandro Medici, Paola Pedrini, Hydroxy group inversion in thiazole polyols by an oxidation-reduction sequence. An entry to syn 1,2-diol fragments in masked carbohydrates The Journal of Organic Chemistry. ,vol. 54, pp. 702- 706 ,(1989) , 10.1021/JO00264A036
Ayumi Takizawa, Kenshu Fujiwara, Eriko Doi, Akio Murai, Hidetoshi Kawai, Takanori Suzuki, Convergent synthesis of the common FGHI-ring part of ciguatoxins Tetrahedron. ,vol. 62, pp. 7408- 7435 ,(2006) , 10.1016/J.TET.2006.05.014
Takashi Yamanoi, Takashi Akiyama, Eiichi Ishida, Hiroyuki Abe, Masahide Amemiya, Toshiyuki Inazu, Horner-Wittig Reaction of Dimethyl 2,3-O-Isopropylidene-D-glyceroylmethylphosphonate and Its Application to the Formal Synthesis of D-erythro-C18-Sphingosine Chemistry Letters. ,vol. 18, pp. 335- 336 ,(1989) , 10.1246/CL.1989.335
Peter Schwab, Robert H. Grubbs, Joseph W. Ziller, Synthesis and Applications of RuCl2(CHR‘)(PR3)2: The Influence of the Alkylidene Moiety on Metathesis Activity Journal of the American Chemical Society. ,vol. 118, pp. 100- 110 ,(1996) , 10.1021/JA952676D
A. Alexakis, D. Jachiet, J.F. Normant, Boron fluoride promoted opening of epoxides by organocopper and cuprate reagents Tetrahedron. ,vol. 42, pp. 5607- 5619 ,(1986) , 10.1016/S0040-4020(01)88165-5
Andre L. Gemal, Jean Louis Luche, Lanthanoids in organic synthesis. 6. Reduction of .alpha.-enones by sodium borohydride in the presence of lanthanoid chlorides: synthetic and mechanistic aspects Journal of the American Chemical Society. ,vol. 103, pp. 5454- 5459 ,(1981) , 10.1021/JA00408A029
M. Pietraszkiewicz, J. Jurczak, Synthesis of chiral diaza-crown ethers incorporating carbohydrate units Tetrahedron. ,vol. 40, pp. 2967- 2970 ,(1984) , 10.1016/S0040-4020(01)91309-2