Abstract
A new synthetic strategy, which allows a complete stereochemical
control of all four chiral centers of two important polyhydroxylated
pyrrolidines 8 and 9 ,
is described. The cornerstone of the present strategy is a successful
implementation of the regioselective asymmetric aminohydroxylation
(RAA) reaction of the designed achiral olefin 1 and
the intramolecular stereoselective amidomercuration reaction of
the δ-alkenylamide 4 , which were used
for the introduction of the vicinal amino alcohol functionality and
for the construction of the five membered ring in the targets respectively.
Key words
carbohydrate - glycosidase inhibitor - polyhydroxylated pyrrolidine - regioselective asymmetric aminohydroxylation reaction - intramolecular
amidomercuration reaction
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