Enantioselective total synthesis and determination of absolute configuration of vittatalactone.
The first asymmetric total synthesis of vittatalactone features the divergent synthesis of two diastereomers to assign the absolute configuration of the natural product. Its consecutive propionate and deoxypropionate stereogenic centers are established by enantioselective o-DPPB directed allylic substitution.
Institut für Organische Chemie und Biochemie, Freiburg Institute for Advanced Studies (FRIAS), Albert-Ludwigs-Universität Freiburg, Alberstr. 21, 79104 Freiburg, Germany.
Yvonne
Y
Schmidt
Bernhard
B
Breit
D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D001517:Coleoptera / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015394:Molecular Structure; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D001688:Biological Products; D007783:Lactones; D012724:Sex Attractants; C497413:vittatalactone