Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 364, Issue 9, Pages 1564-1572Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.202200146
Keywords
biocatalysis; transaminases; aminotetralines; chemoenzymatic
Categories
Funding
- Biotechnology and Biosciences Research Council (BBSRC) [BB/L007444/1]
Ask authors/readers for more resources
Transaminase enzymes have great potential in the synthesis of drugs, and a chemoenzymatic approach for the synthesis of serotonin/melatonin receptor agonists has been developed. Starting from a prochiral ketone compound, both enantiomers of 8-methoxy-2-aminotetraline were obtained in high yields and enantiomeric excesses through stereoselective transamination. These compounds were further converted into either 8-methoxy-2-acetimidotetralines or 8-hydroxy-2-aminodipropyltetralines.
Transaminase enzymes have significant potential for the stereoselective synthesis of drugs or drug precursors. Here, starting from one prochiral beta-tetralone, a short and efficient chemoenzymatic synthesis of four agonists of the serotonin/melatonin receptors have been developed. The key step is the stereoselective transamination of the prochiral ketone to produce both enantiomers of 8-methoxy-2-aminotetraline in high yields and enantiomeric excesses. This was followed by either amidation to give the 8-methoxy-2-acetimidotetralines or several facile chemical steps to the 8-hydroxy-2-aminodipropyltetralines.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available