Enantioselective synthesis of both (-)-(R)-and (+)-(S)-angustureine controlled by enzymatic resolution
The present study describes a new synthesis of (-)-(R)-and (+)-(S)-angustureine enantiomers, as well as of racemate (±)-angustureine, from a racemic β-amino ester controlled by kinetic enzymatic resolution. This strategy allowed to incorporate the basic skeleton, as well as to control the single stereocenter at carbon 2 in both enantiomers. The sequence of five steps starting from the chiral β-amino ester and sodium carboxylate for the synthesis of both alkaloids achieved overall yields of 80 and 44%, respectively, and produced excellent enantiomeric excesses (95 and 96%, respectively) with no protection of functional groups in any of the steps.
Main Authors: | , , |
---|---|
Format: | Digital revista |
Language: | English |
Published: |
Sociedade Brasileira de Química
2013
|
Online Access: | http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532013000900014 |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|