Total synthesis and elucidation of the absolute configuration of the diterpene tonantzitlolone.
[structure: see text] The first enantioselective total synthesis of tonantzitlolone, a novel 15-membered macrocyclic diterpene, utilized a Julia olefination, a highly selective, potassium enolate-based anti-Felkin aldol reaction, and an E-selective ring-closing metathesis as key C-C bond-forming steps. The absolute configuration of tonantzitlolone is established.
Jasper
Christian
C
Institut für Organische Chemie der Universität Hannover, Schneiderberg 1B, D-30167 Hannover, Germany.
Wittenberg
Rüdiger
R
Quitschalle
Monika
M
Jakupovic
Jasmin
J
Kirschning
Andreas
A
D004224:Diterpenes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D047028:Macrocyclic Compounds / Q000138:chemical synthesis*; D008968:Molecular Conformation; D013237:Stereoisomerism; D013816:Thermodynamics
D004224:Diterpenes; D007202:Indicators and Reagents; D047028:Macrocyclic Compounds; C510266:tonantzitlolone