Concise, stereoselective syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid via tandem carbonyl ylide formation-cycloaddition.
[reaction: see text] 1,3-Dipolar cycloaddition of propargyl bromide with the carbonyl ylide derived from 6-diazoheptane-2,5-dione is the key step in concise syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid.
Hodgson
David M
DM
Dyson Perrins Laboratory, Department of Chemistry, University of Oxford, South Parks Road, OX1 3QY, UK. david.hodgson@chem.ox.ac.uk
Avery
Thomas D
TD
Donohue
Andrew C
AC
D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis*; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000494:pharmacology; D008958:Models, Molecular; D010293:Pargyline / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D011763:Pyrrolizidine Alkaloids / Q000138:chemical synthesis* / Q000494:pharmacology; D012674:Senecio / Q000737:chemistry*; D013237:Stereoisomerism
C458240:4-hydroxy-nemorensic acid; D000972:Antineoplastic Agents, Phytogenic; D005663:Furans; D011763:Pyrrolizidine Alkaloids; C458241:nemorensic acid; D010293:Pargyline; C458239:propargyl bromide