Yamashita Shuji, Takeuchi Katsutoshi, Koyama Takuya, Inoue Masayuki, Hayashi Yujiro, Hirama Masahiro
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578 (Japan).
Chemistry. 2015 Feb 2;21(6):2621-8. doi: 10.1002/chem.201405629. Epub 2014 Dec 21.
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/oxidant-sensitive 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.
雪卡毒素是雪卡鱼中毒的主要致病因子，是极大的多环醚类化合物。我们在此报告一种可靠的路线，通过6-外向自由基环化/闭环复分解策略构建CTX1B的左翼，该左翼含有对酸/碱/氧化剂敏感的双烯丙基醚部分。这条新路线使我们能够实现CTX1B的第二代全合成以及54-脱氧CTX1B的首次合成。
