Format:
Online-Ressource
ISSN:
1099-0690
Content:
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.
In:
volume:2014
In:
number:1
In:
year:2013
In:
pages:44-47
In:
extent:4
In:
European journal of organic chemistry, Weinheim : Wiley-VCH Verl., 1998-, 2014, Heft 1 (2013), 44-47 (gesamt 4), 1099-0690
Language:
English
DOI:
10.1002/ejoc.201301257
URN:
urn:nbn:de:101:1-2023011205240742038244
URL:
https://doi.org/10.1002/ejoc.201301257
URL:
https://nbn-resolving.org/urn:nbn:de:101:1-2023011205240742038244
URL:
https://d-nb.info/1277871612/34
URL:
https://doi.org/10.1002/ejoc.201301257
