Co-reporter:Yuuki Ishihara, Nayoung Lee, Naomasa Oshiro, Shigeru Matsuoka, Shuji Yamashita, Masayuki Inoue and Masahiro Hirama
Chemical Communications 2010 vol. 46(Issue 17) pp:2968-2970
Publication Date(Web):05 Mar 2010
DOI:10.1039/B924375E
Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are potent neurotoxic polycyclic ethers. We report herein the total synthesis of a 10-membered F-ring analogue of 51-hydroxyCTX3C, which constitutes the first example of an F-ring modified ciguatoxin that exhibits potent cytotoxicity as well as mouse acute toxicity.
Co-reporter:Shuji Yamashita, Kazuki Kitajima, Kentaro Iso, Masahiro Hirama
Tetrahedron Letters 2009 50(26) pp: 3277-3279
Publication Date(Web):
DOI:10.1016/j.tetlet.2009.02.038
Co-reporter:Yuuki Ishihara, Nayoung Lee, Naomasa Oshiro, Shigeru Matsuoka, Shuji Yamashita, Masayuki Inoue and Masahiro Hirama
Chemical Communications 2010 - vol. 46(Issue 17) pp:NaN2970-2970
Publication Date(Web):2010/03/05
DOI:10.1039/B924375E
Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are potent neurotoxic polycyclic ethers. We report herein the total synthesis of a 10-membered F-ring analogue of 51-hydroxyCTX3C, which constitutes the first example of an F-ring modified ciguatoxin that exhibits potent cytotoxicity as well as mouse acute toxicity.
![Cyclopent[a]indene-5-acetonitrile, 7-chloro-3,3a-dihydro-3,3a-dihydroxy-, (3S,3aR)-](/data/chemimg/3740100/1643768-17-5.png)
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![Cyclopent[a]indene-5-acetonitrile, 4-chloro-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a-dihydro-3a-[(triethylsilyl)oxy]-, (3S,3aR)-](/data/chemimg/3740100/1643768-11-9.png)
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![Cyclopent[a]indene, 4-chloro-5-(chloromethyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a-dihydro-3a-[(triethylsilyl)oxy]-, (3S,3aR)-](/data/chemimg/3740100/1643768-10-8.png)
![Cyclopent[a]indene, 4-chloro-5-(chloromethyl)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a-dihydro-3a-[(triethylsilyl)oxy]-, (3S,3aR)-](/data/chemimg/3740100/1643768-10-8_b.png)
![Cyclopent[a]indene-5-methanol, 4-chloro-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a-dihydro-3a-[(triethylsilyl)oxy]-, 5-methanesulfonate, (3S,3aR)-](/data/chemimg/3740100/1643768-09-5.png)
![Cyclopent[a]indene-5-methanol, 4-chloro-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3,3a-dihydro-3a-[(triethylsilyl)oxy]-, 5-methanesulfonate, (3S,3aR)-](/data/chemimg/3740100/1643768-09-5_b.png)
![Cyclopent[a]indene, 7-chloro-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3,3a-dihydro-3a-[(triethylsilyl)oxy]-, (3S,3aR)-](/data/chemimg/3740100/1643768-07-3.png)
![Cyclopent[a]indene, 7-chloro-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3,3a-dihydro-3a-[(triethylsilyl)oxy]-, (3S,3aR)-](/data/chemimg/3740100/1643768-07-3_b.png)
![Cyclopent[a]indene, 4-chloro-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3,3a-dihydro-3a-[(triethylsilyl)oxy]-, (3S,3aR)-](/data/chemimg/3740100/1643768-05-1.png)
![Cyclopent[a]indene, 4-chloro-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3,3a-dihydro-3a-[(triethylsilyl)oxy]-, (3S,3aR)-](/data/chemimg/3740100/1643768-05-1_b.png)
![Cyclopent[a]indene, 4,7-dichloro-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3,3a-dihydro-3a-[(triethylsilyl)oxy]-, (3S,3aR)-](/data/chemimg/3740100/1643768-03-9.png)
![Cyclopent[a]indene, 4,7-dichloro-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3,3a-dihydro-3a-[(triethylsilyl)oxy]-, (3S,3aR)-](/data/chemimg/3740100/1643768-03-9_b.png)
![Cyclopent[a]indene, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3,3a-dihydro-3a-[(triethylsilyl)oxy]-, (3S,3aR)-](/data/chemimg/3740100/1643768-00-6.png)
![Cyclopent[a]indene, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-3,3a-dihydro-3a-[(triethylsilyl)oxy]-, (3S,3aR)-](/data/chemimg/3740100/1643768-00-6_b.png)
![1-Cyclopentene-1-carboxaldehyde, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-5-[2-[(4R)-2-(4-methoxyphenyl)-4-(2-propyn-1-yl)-1,3-dioxolan-4-yl]ethynyl]-5-[(triethylsilyl)oxy]-, (3R,4S,5S)-](/data/chemimg/3740100/1643767-95-6.png)
![1-Cyclopentene-1-carboxaldehyde, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-5-[2-[(4R)-2-(4-methoxyphenyl)-4-(2-propyn-1-yl)-1,3-dioxolan-4-yl]ethynyl]-5-[(triethylsilyl)oxy]-, (3R,4S,5S)-](/data/chemimg/3740100/1643767-95-6_b.png)
![1-Cyclopentene-1-carboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-5-[2-[(4R)-2-(4-methoxyphenyl)-4-(2-propyn-1-yl)-1,3-dioxolan-4-yl]ethynyl]-5-[(triethylsilyl)oxy]-, methyl ester, (3R,4S,5S)-](/data/chemimg/3740100/1643767-94-5.png)
![1-Cyclopentene-1-carboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-5-[2-[(4R)-2-(4-methoxyphenyl)-4-(2-propyn-1-yl)-1,3-dioxolan-4-yl]ethynyl]-5-[(triethylsilyl)oxy]-, methyl ester, (3R,4S,5S)-](/data/chemimg/3740100/1643767-94-5_b.png)
![1-Cyclopentene-1-carboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-5-[2-[(4R)-2-(4-methoxyphenyl)-4-[3-(trimethylsilyl)-2-propyn-1-yl]-1,3-dioxolan-4-yl]ethynyl]-5-[(triethylsilyl)oxy]-, methyl ester, (3R,4S,5S)-](/data/chemimg/3740100/1643767-93-4.png)
![1-Cyclopentene-1-carboxylic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-5-[2-[(4R)-2-(4-methoxyphenyl)-4-[3-(trimethylsilyl)-2-propyn-1-yl]-1,3-dioxolan-4-yl]ethynyl]-5-[(triethylsilyl)oxy]-, methyl ester, (3R,4S,5S)-](/data/chemimg/3740100/1643767-93-4_b.png)
![1,3-Dioxolane, 4-[2-[(1R,4R,5S)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-iodo-4-[(4-methoxyphenyl)methoxy]-1-[(triethylsilyl)oxy]-2-cyclopenten-1-yl]ethynyl]-2-(4-methoxyphenyl)-4-[3-(trimethylsilyl)-2-propyn-1-yl]-, (4R)-](/data/chemimg/3740100/1643767-92-3.png)
![1,3-Dioxolane, 4-[2-[(1R,4R,5S)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-iodo-4-[(4-methoxyphenyl)methoxy]-1-[(triethylsilyl)oxy]-2-cyclopenten-1-yl]ethynyl]-2-(4-methoxyphenyl)-4-[3-(trimethylsilyl)-2-propyn-1-yl]-, (4R)-](/data/chemimg/3740100/1643767-92-3_b.png)
![2-Cyclopenten-1-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-iodo-4-[(4-methoxyphenyl)methoxy]-1-[2-[(4R)-2-(4-methoxyphenyl)-4-[3-(trimethylsilyl)-2-propyn-1-yl]-1,3-dioxolan-4-yl]ethynyl]-, (1R,4R,5S)-](/data/chemimg/3740100/1643767-91-2.png)
![2-Cyclopenten-1-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-iodo-4-[(4-methoxyphenyl)methoxy]-1-[2-[(4R)-2-(4-methoxyphenyl)-4-[3-(trimethylsilyl)-2-propyn-1-yl]-1,3-dioxolan-4-yl]ethynyl]-, (1R,4R,5S)-](/data/chemimg/3740100/1643767-91-2_b.png)
![2-Cyclopenten-1-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-hydroxy-2-iodo-, (4R,5S)-](/data/chemimg/3740100/1643767-90-1.png)
![2-Cyclopenten-1-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4-hydroxy-2-iodo-, (4R,5S)-](/data/chemimg/3740100/1643767-90-1_b.png)
![1,5-Hexadiyn-3-ol, 3-[[(4-methoxyphenyl)methoxy]methyl]-6-(trimethylsilyl)-, (3R)-](/data/chemimg/3740100/1643767-89-8.png)
![1,5-Hexadiyn-3-ol, 3-[[(4-methoxyphenyl)methoxy]methyl]-6-(trimethylsilyl)-, (3R)-](/data/chemimg/3740100/1643767-89-8_b.png)
![D-threo-Pent-1-ynitol, 3,4-anhydro-1,2-dideoxy-4-C-ethynyl-5-O-[(4-methoxyphenyl)methyl]-1-(trimethylsilyl)-](/data/chemimg/3740100/1643767-88-7.png)
![D-threo-Pent-1-ynitol, 3,4-anhydro-1,2-dideoxy-4-C-ethynyl-5-O-[(4-methoxyphenyl)methyl]-1-(trimethylsilyl)-](/data/chemimg/3740100/1643767-88-7_b.png)
![1,3-Dioxolane, 4-ethynyl-2-(4-methoxyphenyl)-4-[3-(trimethylsilyl)-2-propyn-1-yl]-, (2S,4R)-](/data/chemimg/3740100/1643767-85-4.png)
![1,3-Dioxolane, 4-ethynyl-2-(4-methoxyphenyl)-4-[3-(trimethylsilyl)-2-propyn-1-yl]-, (2S,4R)-](/data/chemimg/3740100/1643767-85-4_b.png)
![1,3-Dioxolane, 4-ethynyl-2-(4-methoxyphenyl)-4-[3-(trimethylsilyl)-2-propyn-1-yl]-, (2R,4R)-](/data/chemimg/3740100/1643767-84-3.png)
![1,3-Dioxolane, 4-ethynyl-2-(4-methoxyphenyl)-4-[3-(trimethylsilyl)-2-propyn-1-yl]-, (2R,4R)-](/data/chemimg/3740100/1643767-84-3_b.png)
![2-Cyclopenten-1-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-iodo-4-[(4-methoxyphenyl)methoxy]-, (4R,5S)-](/data/chemimg/3740100/1643767-83-2.png)
![2-Cyclopenten-1-one, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-iodo-4-[(4-methoxyphenyl)methoxy]-, (4R,5S)-](/data/chemimg/3740100/1643767-83-2_b.png)
![Cyclopent[a]indene-5-acetonitrile, 3-(acetyloxy)-7-chloro-3,3a-dihydro-3a-hydroxy-, (3S,3aR)-](/data/chemimg/3739900/1423138-35-5.png)
![Cyclopent[a]indene-5-acetonitrile, 3-(acetyloxy)-7-chloro-3,3a-dihydro-3a-hydroxy-, (3S,3aR)-](/data/chemimg/3739900/1423138-35-5_b.png)
![5H-Dibenzo[b,j][1,5]dioxacycloundecin-5-one, 7,8-dihydro-8,14-dihydroxy-4-methyl-7-pentyl-, (7S,8R,9E)-](/data/chemimg/3739800/796086-18-5.png)
![5H-Dibenzo[b,j][1,5]dioxacycloundecin-5-one, 7,8-dihydro-8,14-dihydroxy-4-methyl-7-pentyl-, (7S,8R,9E)-](/data/chemimg/3739800/796086-18-5_b.png)
![1,3,2-Dioxaborolane, 2-[(1E,3S)-3,4-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-buten-1-yl]-4,5-dimethyl-](/data/chemimg/3739800/676609-77-1.png)
![1,3,2-Dioxaborolane, 2-[(1E,3S)-3,4-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-buten-1-yl]-4,5-dimethyl-](/data/chemimg/3739800/676609-77-1_b.png)
![4H-1,3-Dioxino[5,4-b]oxepin-6-methanol, 4a,8,9,9a-tetrahydro-2-(4-methoxyphenyl)-, (2R,4aR,9aS)-](/data/chemimg/3739800/568572-13-4.png)
![4H-1,3-Dioxino[5,4-b]oxepin-6-methanol, 4a,8,9,9a-tetrahydro-2-(4-methoxyphenyl)-, (2R,4aR,9aS)-](/data/chemimg/3739800/568572-13-4_b.png)
![4H-1,3-Dioxino[5,4-b]oxepin-6-carboxylic acid, 4a,8,9,9a-tetrahydro-2-(4-methoxyphenyl)-, methyl ester, (2R,4aR,9aS)-](/data/chemimg/3739800/568572-12-3.png)
![4H-1,3-Dioxino[5,4-b]oxepin-6-carboxylic acid, 4a,8,9,9a-tetrahydro-2-(4-methoxyphenyl)-, methyl ester, (2R,4aR,9aS)-](/data/chemimg/3739800/568572-12-3_b.png)
![2-Cyclopenten-1-one, 4-(acetyloxy)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-iodo-, (4R,5S)-](/data/chemimg/3739800/361482-73-7.png)
![2-Cyclopenten-1-one, 4-(acetyloxy)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-iodo-, (4R,5S)-](/data/chemimg/3739800/361482-73-7_b.png)
![Phenol,2,4-bis(1,1-dimethylethyl)-6-[(E)-[[(1S)-1-(hydroxymethyl)-2-methylpropyl]imino]phenylmethyl]-](http://img.cochemist.com/ccimg/210700/210626-68-9.png)
![Phenol,2,4-bis(1,1-dimethylethyl)-6-[(E)-[[(1S)-1-(hydroxymethyl)-2-methylpropyl]imino]phenylmethyl]-](http://img.cochemist.com/ccimg/210700/210626-68-9_b.png)
![Benzene, 1-[(S)-ethynylsulfinyl]-4-methyl-](http://img.cochemist.com/ccimg/195100/195063-98-0.png)
![Benzene, 1-[(S)-ethynylsulfinyl]-4-methyl-](http://img.cochemist.com/ccimg/195100/195063-98-0_b.png)
![(2R,2'R,3a'S,4a'R,5'S,6'S,6a'S,9'S,10'S,10a'R,11a'S,12a'R,13a'S,14a'R,15a'S,17'E,19a'R,20a'S,22a'R,23a'S,24'R,24a'R,26'R,29a'S,30a'R,31a'S,32a'R,34a'S,35a'R,37'R,37a'S,38a'R)-26'-[(1E,3S)-3,4-dihydroxybut-1-en-1-yl]-2',5',9',10',37a'-pentamethyl-1',3',3a'](http://img.cochemist.com/ccimg/139400/139341-09-6.png)
![(2R,2'R,3a'S,4a'R,5'S,6'S,6a'S,9'S,10'S,10a'R,11a'S,12a'R,13a'S,14a'R,15a'S,17'E,19a'R,20a'S,22a'R,23a'S,24'R,24a'R,26'R,29a'S,30a'R,31a'S,32a'R,34a'S,35a'R,37'R,37a'S,38a'R)-26'-[(1E,3S)-3,4-dihydroxybut-1-en-1-yl]-2',5',9',10',37a'-pentamethyl-1',3',3a'](http://img.cochemist.com/ccimg/139400/139341-09-6_b.png)
![L-arabino-Hexopyranosyl fluoride, 2,6-dideoxy-4-O-[2,6-dideoxy-4-O-[(1,1-dimethylethyl)dimethylsilyl]-3-O-methyl-α-L-arabino-hexopyranosyl]-3-O-methyl-](/data/chemimg/3739800/135635-95-9.png)
![L-arabino-Hexopyranosyl fluoride, 2,6-dideoxy-4-O-[2,6-dideoxy-4-O-[(1,1-dimethylethyl)dimethylsilyl]-3-O-methyl-α-L-arabino-hexopyranosyl]-3-O-methyl-](/data/chemimg/3739800/135635-95-9_b.png)
![L-arabino-Hex-1-enitol, 1,5-anhydro-2,6-dideoxy-4-O-[(1,1-dimethylethyl)dimethylsilyl]-3-O-methyl-](/data/chemimg/3739800/117452-74-1.png)
![L-arabino-Hex-1-enitol, 1,5-anhydro-2,6-dideoxy-4-O-[(1,1-dimethylethyl)dimethylsilyl]-3-O-methyl-](/data/chemimg/3739800/117452-74-1_b.png)
![L-arabino-Hex-1-enitol, 1,5-anhydro-2,6-dideoxy-4-O-[(1,1-dimethylethyl)dimethylsilyl]-, 3-benzoate](/data/chemimg/3739800/117452-73-0.png)
![L-arabino-Hex-1-enitol, 1,5-anhydro-2,6-dideoxy-4-O-[(1,1-dimethylethyl)dimethylsilyl]-, 3-benzoate](/data/chemimg/3739800/117452-73-0_b.png)
![1,7-Dioxaspiro[5.5]undec-10-ene-2-ethanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9-methyl-8-[(1S)-1-methylpropyl]-, (2R,4S,6S,8R,9S)-](/data/chemimg/3739800/105286-14-4.png)
![1,7-Dioxaspiro[5.5]undec-10-ene-2-ethanol, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-9-methyl-8-[(1S)-1-methylpropyl]-, (2R,4S,6S,8R,9S)-](/data/chemimg/3739800/105286-14-4_b.png)
![Benzene, 1-[(R)-ethynylsulfinyl]-4-methyl-](http://img.cochemist.com/ccimg/100000/99930-83-3.png)
![Benzene, 1-[(R)-ethynylsulfinyl]-4-methyl-](http://img.cochemist.com/ccimg/100000/99930-83-3_b.png)
![α-L-arabino-Hexopyranoside, phenyl 2,6-dideoxy-4-O-[2,6-dideoxy-4-O-[(1,1-dimethylethyl)dimethylsilyl]-3-O-methyl-α-L-arabino-hexopyranosyl]-3-O-methyl-1-thio-](/data/chemimg/3739800/90670-41-0.png)
![α-L-arabino-Hexopyranoside, phenyl 2,6-dideoxy-4-O-[2,6-dideoxy-4-O-[(1,1-dimethylethyl)dimethylsilyl]-3-O-methyl-α-L-arabino-hexopyranosyl]-3-O-methyl-1-thio-](/data/chemimg/3739800/90670-41-0_b.png)
![OXIRANE, 3-[(3E)-5-CHLORO-3-METHYL-3-PENTENYL]-2,2-DIMETHYL-](http://img.cochemist.com/ccimg/43200/43119-82-0.png)
![OXIRANE, 3-[(3E)-5-CHLORO-3-METHYL-3-PENTENYL]-2,2-DIMETHYL-](http://img.cochemist.com/ccimg/43200/43119-82-0_b.png)
![Phosphonothioic acid,P-methyl-, S-[2-(diethylamino)ethyl] ester](http://img.cochemist.com/ccimg/21100/21068-51-9.png)
![Phosphonothioic acid,P-methyl-, S-[2-(diethylamino)ethyl] ester](http://img.cochemist.com/ccimg/21100/21068-51-9_b.png)
![Hexanamide,N-[4-[(hydroxyamino)sulfonyl]phenyl]-](http://img.cochemist.com/ccimg/7000/6937-32-2.png)
![Hexanamide,N-[4-[(hydroxyamino)sulfonyl]phenyl]-](http://img.cochemist.com/ccimg/7000/6937-32-2_b.png)
![3-Penten-2-one,5-(3,3-dimethylbicyclo[2.2.1]hept-2-ylidene)-](http://img.cochemist.com/ccimg/2300/2226-11-1.png)
![3-Penten-2-one,5-(3,3-dimethylbicyclo[2.2.1]hept-2-ylidene)-](http://img.cochemist.com/ccimg/2300/2226-11-1_b.png)
