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Straightforward Synthesis of All Stenusine and Norstenusine Stereoisomers
Author(s) -
Müller Tobias,
Dettner Konrad,
Seifert Karlheinz
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.201100612
Subject(s) - chemistry , yield (engineering) , reagent , combinatorial chemistry , stereochemistry , organic chemistry , metallurgy , materials science
All the stereoisomers of stenusine ( 1 ) and norstenusine ( 21 ) have been efficiently synthesized by the asymmetric hydrogenation of pyridines. The (2 R ,3 S )‐ and (2 R ,3 R )‐isomers of 1 , that are difficult to prepare, have been synthesized for the first time using a chemoenzymatic approach in eight steps with an 8 % total yield. All the target compounds were obtained in good stereochemical purity by using very simple and inexpensive reagents and auxiliaries.