Flexibility in the partial reduction of 2,5-disubstituted pyrroles: application to the synthesis of DMDP.
[reaction: see text] The partial reduction of electron-deficient 2,5-disubstituted pyrroles has been developed into a flexible procedure that gives control of relative stereochemistry by variation of the reduction conditions. After the reaction, the pyrroline products were dihydroxylated at C-3,4 to give either the cis or trans isomers; this flexibility means that a variety of polyhydroxylated pyrrolidines can be prepared in a short sequence. Finally, this method was applied to a synthesis of the naturally occurring glycosidase inhibitor DMDP.
Donohoe
Timothy J
TJ
Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, United Kingdom.
Headley
Catherine E
CE
Cousins
Rick P C
RP
Cowley
Andrew
A
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D050113:Imino Furanoses; D007536:Isomerism; D008353:Mannitol / Q000031:analogs & derivatives; D015394:Molecular Structure; D011758:Pyrroles / Q000737:chemistry*; D011759:Pyrrolidines
D000470:Alkaloids; D004791:Enzyme Inhibitors; D050113:Imino Furanoses; D011758:Pyrroles; D011759:Pyrrolidines; D008353:Mannitol; C043121:2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine; D006026:Glycoside Hydrolases