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- Title
Synthesis of All the Diastereomers of 2-Amino-3-hydroxy-4,5-dimethylhexanoic Acid.
- Authors
Spengler, Jan; Albericio, Fernando
- Abstract
Herein, we describe an efficient stereoselective synthesis of all the diastereomers of 2-amino-3-hydroxy-4,5-dimethylhexanoic acid. The γ-branched carbon skeleton was set up by reaction of Garner's aldehyde with 2-lithio-3-methyl-2-butene. Hydrogenation (Pd/C catalyst) of the tetrasubstituted olefin proceeded smoothly with acceptable stereoselectivity, depending on the diastereomer hydrogenated. The final compounds were then obtained in 12-18 % overall yield through intramolecular cyclization, Jones oxidation, and hydrolysis in 5-7 steps from Garner's aldehyde.
- Subjects
DIASTEREOISOMERS synthesis; AMINO acid synthesis; HYDROGENATION; CATALYST synthesis; STEREOSELECTIVE reactions; RING formation (Chemistry); OXIDATION; HYDROLYSIS
- Publication
European Journal of Organic Chemistry, 2014, Vol 2014, Issue 1, p44
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201301257