Total synthesis of cyclic diterpene tonantzitlolone based on a highly stereoselective substrate-controlled aldol reaction and ring-closing metathesis.
The total synthesis of the cyclic diterpene ent-tonantzitlolone (ent-1) is presented. Key steps for assembling the macrocyclic core structure of 1 are a highly selective aldol reaction and an E selective ring-closing metathesis reaction. A detailed investigation of these two steps and the final transformations towards the completion of the synthesis is disclosed.
Jasper
Christian
C
Universität Basel, Departement Chemie, Spitalstrasse 51, 4065 Basel, Switzerland.
Adibekian
Alexander
A
Busch
Torsten
T
Quitschalle
Monika
M
Wittenberg
Rüdiger
R
Kirschning
Andreas
A
D003500:Cyclization; D004224:Diterpenes / Q000138:chemical synthesis*; D047028:Macrocyclic Compounds / Q000138:chemical synthesis*; D008956:Models, Chemical; D013237:Stereoisomerism
D004224:Diterpenes; D047028:Macrocyclic Compounds; C510266:tonantzitlolone