The electron-releasing homoconjugated carbonyl group. Application to the total syntheses of 3-deoxy-, 4-deoxy-hexose, lividosamine and derivatives |
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| Authors: | Daniela Fattori Etienne de Guchteneere and Pierre Vogel |
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| Institution: | Institut de chimie organique de l'Université, 2, rue de la Barre, CH-1005 Lausanne, Switzerland |
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| Abstract: | The regioselective electrophilic addition of benzeneselenyl bromide to (−)-(1S,4S)-7-oxabicyclo2.2.1]-hept-5-en-2-one were exploited to develop efficient syntheses of methyl 3-deoxy- -D-arabino-hexofuranoside and 4-deoxy-D-lyxo-hexopyranose. Similarly, D-lividosamine (3-deoxy-D-glucosamine) was derived from (+)-(1R,4R)-7-oxabicyclo2.2.1]hept-5-en-2-one. |
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