TY - JOUR
T1 - Practical route to the left wing of CTX1B and total syntheses of CTX1B and 54-deoxyCTX1B
AU - Yamashita, Shuji
AU - Takeuchi, Katsutoshi
AU - Koyama, Takuya
AU - Inoue, Masayuki
AU - Hayashi, Yujiro
AU - Hirama, Masahiro
N1 - Publisher Copyright:
© 2015 Wiley-VCH Verlag GmbH & Co. KGaA.
PY - 2015/2/2
Y1 - 2015/2/2
N2 - Ciguatoxins, the principal causative agents of ciguatera seafood poisoning, are extremely large polycyclic ethers. We report herein a reliable route for constructing the left wing of CTX1B, which possesses the acid/base/oxidantsensitive bisallylic ether moiety, by a 6-exo radical cyclization/ring-closing metathesis strategy. This new route enabled us to achieve the second-generation total synthesis of CTX1B and the first synthesis of 54-deoxyCTX1B.
AB - Ciguatoxins, the principal causative agents of ciguatera seafood poisoning, are extremely large polycyclic ethers. We report herein a reliable route for constructing the left wing of CTX1B, which possesses the acid/base/oxidantsensitive bisallylic ether moiety, by a 6-exo radical cyclization/ring-closing metathesis strategy. This new route enabled us to achieve the second-generation total synthesis of CTX1B and the first synthesis of 54-deoxyCTX1B.
KW - Ciguatoxin
KW - Polycyclic ether
KW - Radical reaction
KW - Ring-closing metathesis
KW - Total synthesis
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U2 - 10.1002/chem.201405629
DO - 10.1002/chem.201405629
M3 - Article
C2 - 25529606
AN - SCOPUS:84921691142
VL - 21
SP - 2621
EP - 2628
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 6
ER -