Catalytic and asymmetric vinylogous mukaiyama reactions on aliphatic ketones: formal asymmetric synthesis of taurospongin a.
Catalytic asymmetric vinylogous Mukaiyama reactions on ketones, leading to the formation of alpha,beta-unsaturated lactones with tertiary alcohols, have been described (11 examples, up to 93% ee). This methodology has been applied in a formal enantioselective synthesis of taurospongin A (12 steps, 6% overall yield).
Moreau
Xavier
X
Institut de Chimie des Substances Naturelles, CNRS, Gif-sur-Yvette, France.
Bazán-Tejeda
Belen
B
Campagne
Jean-Marc
JM
D000480:Alkynes / Q000138:chemical synthesis*; D000818:Animals; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*; D011161:Porifera / Q000737:chemistry; D014753:Vinyl Compounds / Q000737:chemistry*
D000480:Alkynes; D004952:Esters; D007659:Ketones; D014753:Vinyl Compounds; C464964:taurospongin A