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Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Flexibility in the partial reduction of 2,5-disubstituted pyrroles: application to the synthesis of DMDP
Timothy J Donohoe1, Catherine E Headley, Rick P C Cousins
1Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, United Kingdom.
Abstract:
[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.
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