Total Synthesis of (−)-Tetrodotoxin from d -Glucose: A New Route to Multi-Functionalized Cyclitol Employing the Ferrier(II) Reaction toward (−)-Tetrodotoxin
2010; Oxford University Press; Volume: 83; Issue: 3 Linguagem: Inglês
10.1246/bcsj.20090194
ISSN1348-0634
AutoresShoji Akai, Hidehito Seki, Naoki Sugita, Tomokazu Kogure, Naoki Nishizawa, Katsuhiko Suzuki, Yutaka Nakamura, Yasuhiro Kajihara, Juji Yoshimura, Ken‐ichi Sato,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoAbstract Total synthesis of (−)-tetrodotoxin (TTX) from d-glucose is described. As a critical transformation step for synthesizing TTX, a key multi-functionalized cyclitol was prepared from d-glucose employing the Ferrier(II) reaction. Stereospecific introduction of three functionalized branched chains were achieved via Peterson olefination and spiro α-chloroepoxidation of the corresponding carbonyl derivatives.
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