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Tetrodotoxin - Recent Asymmetric Syntheses A Hinman J Du...

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O AcO NHAc OH O O OH HO OH NH HN H 2 N HO (-)-tetrodotoxin acid ox. state ketone ox. state OH O O HO OH N carbonic ester ox. state NH 2 H 2 N O OH OH OAc O O AcO OAc AcHN O OAc AcO OAc OH O AcO O AcHN O OAc AcO dihydroxlation and cleavage epoxide opening CO 2 H O O Ac AcO O AcO NHAc O O O Ac AcO OAc rotate 120° O AcO NHAc O AcO H H H OR epoxidation O NHAc Me H O O O Me O NHAc O O O H SeO 2 allylic oxidation Baeyer-Villager ox epoxide opening Me O O quinone Diels-Alder rxn Me O O Me O NHAc O H O + N OH Me O O NHAc H N OH electronics are not well suited for Diels-Alder Kishi's Synthesis of Tetrodotoxin: An Exercise in Selective Oxidation Chemistry
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Unformatted text preview: Recent Asymmetric Syntheses: A. Hinman, J. Du Bois J. Am. Chem. Soc. 2003 , 11510. T. Nishikawa, D. Urabe, M. Isobe J. Am. Chem. Soc. 2003 , 8798. First Total Synthesis: Y. Kishi,* M. Aratani, T. Fukuyama, F. Nakatsubo, T. Goto, S. Inoue, H. Tanino, S. Sugiura, H. Kakoi. J. Am. Chem. Soc. 1972 , 9217; J. Am. Chem. Soc. 1972 , 9219. Beckmann rearrangement Reisman, 242a...
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