Stereospecific synthesis of (−)- allo-muscarine from d-glucose (original) (raw)

Carbohydrate Research, 1996

Abstract

ABSTRACT The key chiral synthon in a novel synthesis of (-)- allo -muscarine from D-glucose has been prepared by three independent routes. The most efficient one includes a four-step conversion via the 4- O -benzoyl derivatives of starting 2,5-anhydro-3,5-di- O -methanesulfonyl-L-idose ethylene acetal ( 2a ) into 2,5-anhydro-3,6-dideoxy-L- lyxo- hexose ethylene acetal ( 4b ). The intermediate 4b was efficiently converted into the chiral synthon 2,5-anhydro-4- O -benzoyl-3,6-dideoxy-L- arabino -hexose ( 4c ) by Mitsunobu reaction.

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