The first enantioselective synthesis of palinurin.
The first enantioselective synthesis of palinurin has been accomplished starting from commercially available furaldehyde and (R)-methyl-3-hydroxy-2-methylpropionate; the key steps of the synthesis include the use of a chiral pyrrolidine to create the chiral tetronic moiety, and Horner-Wadsworth-Emmons, Wittig and Wittig-Horner reactions to construct the alkene units.
Pérez
Manuel
M
Departamento de Química Orgánica, Facultad de Química, Universidad de Vigo, 36200 Vigo, Spain.
Pérez
Daniel I
DI
Martínez
Ana
A
Castro
Ana
A
Gómez
Generosa
G
Fall
Yagamare
Y
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D010720:Phosphines / Q000737:chemistry; D011422:Propionates / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D000447:Aldehydes; D005663:Furans; D010720:Phosphines; D011422:Propionates; D013729:Terpenes; C542546:palinurin; C044646:phosphine; D015107:4-Butyrolactone; C039281:furan