Stereoselective and Efficient Total Synthesis of Optically Active Tetrodotoxin from d-Glucose
The Journal of Organic Chemistry2008Vol. 73(4), pp. 1234–1242
Citations Over TimeTop 10% of 2008 papers
Ken‐ichi Sato, Shoji Akai, Hirotsugu Shoji, Naoki Sugita, Shiho Yoshida, Yoshinao Nagai, Katsuhiko Suzuki, Yutaka Nakamura, Yasuhiro Kajihara, Masuo Funabashi, Juji Yoshimura
Abstract
A stereoselective and efficient total synthesis of optically active tetrodotoxin (TTX) is described. A polyfunctionalized key cyclitol compound containing branched-chains for the synthesis of TTX was prepared from D-glucose employing the Henry reaction (Nitro aldol reaction) as the key transformation. Stereoselective construction of the alpha-azido-aldehyde branched-chain was achieved via the key spiro alpha-chloroepoxide intermediate.
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