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A practical synthesis of Kdn2en and 4-amino-4-deoxy-Kdn2en has been achieved via a key intermediate, methyl 4,5,7,8,9-penta-O-acetyl-2,6-anhydro-3-deoxy-d-glycero-d-galacto-non-2-enona te, which has been prepared from Kdn in three steps in 91% overall yield.
Methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-2,6-anhydro-3,4-dideoxy-d-glycero-d-galac to- and d-talo-non-2-enonates were synthesized from the reaction of the peracetate of Kdn methyl ester with several nitriles in the presence of a Lewis acid. Treatment of these 2,4-dideoxy-4-acylamino-Kdn methyl esters with N-bromosuccinimide in methanol gave methyl (methyl 5,7,8,9-tetra-O-acetyl-4-acylamino-3-bromo-3,4-dideoxy-d-erythro-α-l-manno-...
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