Synthesis of the ABCDEF-ring of ciguatoxin 3C

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• 作者：Takuto Sato^a ; Kenshu Fujiwara^b ; ^{fjwkn@gipc.akita-u.ac.jp} ; Keisuke Nogoshi^a ; Akiyoshi Goto^a ; Daisuke Domon^a ; Natsumi Kawamura^a ; Yoshitaka Nomura^a ; Daisuke Sato^a ; Hideki Tanaka^a ; Akio Murai^a ; Yoshihiko Kondo^b ; Uichi Akiba^b ; Ryo Katoono^a ; Hidetoshi Kawai^a ; Takanori Suzuki^a
• 关键词：Natural product synthesis ; Fused polycyclic ethers ; Ireland-Claisen rearrangement ; Ring closing olefin metathesis ; Stereoselective synthesis
• 刊名：Tetrahedron
• 出版年：2017
• 出版时间：9 February 2017
• 年：2017
• 卷：73
• 期：6
• 页码：703-726
• 全文大小：2127 K
• 卷排序：73

文摘

The synthesis of the ABCDEF-ring of ciguatoxin 3C was achieved via a route that included anion coupling of a dimethyldithioacetal mono-S-oxide derivative corresponding to the AB-ring and an aldehyde corresponding to the EF-ring, followed by cyclization using reductive etherification. The AB-ring was synthesized from a known d-glucose derivative based on ring-closing olefin metathesis, and the EF-ring was prepared by a process employing chirality-transferring Ireland-Claisen rearrangement and ring-closing olefin metathesis.