Premium
Diastereoselective Synthesis of Lincosamine Precursors
Author(s) -
Serra Fiona,
Coutrot Philippe,
EstèveQuelquejeu Mélanie,
Herson Patrick,
Olszewski Tomasz K.,
Grison Claude
Publication year - 2011
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.201001740
Subject(s) - chemistry , diastereomer , amination , stereoselectivity , reductive amination , nucleophile , pyranose , stereochemistry , nucleophilic addition , organic chemistry , catalysis
The stereoselective syntheses of the four aminodiol precursors of the diastereomers of lincosamine are reported. The procedure is based on the initial two‐carbon elongationof 1,2;3,4‐di‐ O ‐isopropylidene‐α‐ D ‐galactohexodialdo‐1,5‐pyranose, followed by the stereocontrolled introduction of the amino group by nucleophilic amination. Two complementary approaches have been investigated and compared: The first one is the direct transformation of α‐chloroglycidic ester into β‐amino‐α‐keto ester. The second strategy is a three‐step synthesis that is based on the treatment of the β‐iodo‐α‐keto ester with dibenzylamine. Subsequent reduction of the β‐amino‐α‐keto ester provides the pure D ‐ erythro , L ‐ threo , L ‐ erythro , and D ‐ threo aminodiols after chromatographic purification. Further classical transformations afford the N ‐acetyl derivatives, which are key precursors of the lincosamine diastereomers.