Formal total synthesis of (+)-gephyrotoxin.
An efficient formal total synthesis of (+)-gephyrotoxin is described. The key step of our strategy relies on the diastereoselective reduction of a chiral pyrrolidine beta-enamino ester obtained by condensation of ( S)-phenylglycinol on a protected 8-hydroxy-3,6-dioxooctanoate.
Santarem
Marco
M
UPMC Univ Paris 06, CNRS, UMR 7611, Laboratoire de Chimie Organique, Equipe Chimie des Hétérocycles, 4 Place Jussieu, F-75005 Paris, France.
Vanucci-Bacqué
Corinne
C
Lhommet
Gérard
G
D000470:Alkaloids / Q000138:chemical synthesis*; D000664:Amphibian Venoms / Q000138:chemical synthesis; D004983:Ethanolamines; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000470:Alkaloids; D000664:Amphibian Venoms; D004983:Ethanolamines; D011759:Pyrrolidines; C014569:gephyrotoxin; C005332:N-phenylethanolamine; D005998:Glycine