Stereocontrolled synthesis of 8,11-dideoxytetrodotoxin,unnatural analogue of puffer fish toxin |
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Authors: | Nishikawa Toshio Urabe Daisuke Yoshida Kazumasa Iwabuchi Tomoko Asai Masanori Isobe Minoru |
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Affiliation: | Laboratory of Organic Chemistry, Graduate School of Bioagricultural Sciences, Nagoya University, Chikusa, Japan. |
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Abstract: | ![]() [structure: see text] 8,11-Dideoxytetrodotoxin, an unnatural tetrodotoxin analogue, was synthesized in a highly stereoselective manner from a common intermediate in our synthetic studies on tetrodotoxin. The synthesis features neighboring group participation of trichloroacetamide for stereoselective hydroxylation, protection of ortho ester, and guanidine installation with Boc-protected isothiourea. |
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