Total synthesis of (+)-bourgeanic acid utilizing o-DPPB-directed allylic substitution.
The lichen metabolite (+)-bourgeanic acid has been synthesized utilizing a new strategy for the construction of propionate motifs relying on the o-DPPB-directed copper-mediated allylic substitution. This synthesis features the o-DPPB-directed allylic substitution employing a chiral Grignard reagent, Sharpless asymmetric epoxidation, and reductive epoxide ring opening with a higher order dimethylcuprate to set the four stereogenic centers of the aliphatic depside.
Reiss
Tomislav
T
Institut für Organische Chemie und Biochemie, Freiburg Institute for Advanced Studies, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, 79115 Freiburg, Germany.
Breit
Bernhard
B
D000473:Alkanes / Q000138:chemical synthesis*; D001565:Benzoates / Q000737:chemistry; D001713:Biphenyl Compounds / Q000737:chemistry; D008011:Lichens / Q000737:chemistry / Q000378:metabolism*; D011422:Propionates / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000473:Alkanes; D001565:Benzoates; D001713:Biphenyl Compounds; D011422:Propionates; C544845:bourgeanic acid; C544846:o-diphenylphosphanylbenzoyl