Highly enantioselective total synthesis of (-)-(3'S)-Lomatin and (+)-(3'S,4'R)-trans-khellactone.
Concise highly enantioselective three-step syntheses are described for (-)-(3'S)-lomatin and (+)-(3'S,4'R)-trans-khellactone from 7-hydroxycoumarin in 97% ee and in 57% and 58% overall yields, respectively, using nonaqueous enantioselective epoxidation by an iminium salt as the key step.
Page
Philip C Bulman
PC
School of Chemistry, University of East Anglia, University Plain, Norwich, Norfolk NR4 7TJ, UK. p.page@uea.ac.uk
Appleby
Louise F
LF
Day
David
D
Chan
Yohan
Y
Buckley
Benjamin R
BR
Allin
Steven M
SM
McKenzie
Michael J
MJ
D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry*; D018360:Crystallography, X-Ray; D015394:Molecular Structure; D013237:Stereoisomerism; D014468:Umbelliferones / Q000737:chemistry
D003374:Coumarins; D014468:Umbelliferones; C540381:lomatin; C031477:7-hydroxycoumarin; C520900:khellactone