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Chemoenzymatic Synthesis of δ‐Keto β‐Hydroxy Esters as Useful Intermediates for Preparing Statins
Author(s) -
Tartaggia Stefano,
Fogal Stefano,
Motterle Riccardo,
Ferrari Clark,
Pontini Marta,
Aureli Roberto,
De Lucchi Ottorino
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600268
Subject(s) - chemistry , enantiopure drug , rosuvastatin , aldol reaction , combinatorial chemistry , chemical synthesis , enantioselective synthesis , organic chemistry , catalysis , biochemistry , medicine , in vitro
Enantiopure ( R )‐3‐hydroxy‐5‐oxohexanoic acid esters have proven to be useful intermediates in the synthesis of the side chain of statins, in view of the recently described preparation of rosuvastatin and other statins through aldol reactions. Herein, an improved synthesis of these intermediates, by combining chemical and enzymatic reactions, is described. In particular, the selective reduction of a δ‐ketal β‐keto ester was identified as a key step to obtain derivatives with satisfactory optical purities for use in the synthesis of statins.