The total synthesis of (+)-tedanolide.
The first total synthesis of the (+)-tedanolide is described. Pivotal steps are the Felkin-selective aldol coupling between C12 and C13 and an efficient Mitsunobu macrolactonization. Selective protecting group transformations and subsequent oxidations generate the macrocyclic triketone. In the endgame of the synthesis, four TBS groups are removed in one reaction and a chemo- and stereoselective final step epoxidation generates (+)-tedanolide.
Ehrlich
Gunnar
G
Institut für Organische Chemie, Leibniz Universität Hannover, Schneiderberg 1B, D-30167 Hannover, Germany.
Hassfeld
Jorma
J
Eggert
Ulrike
U
Kalesse
Markus
M
D007783:Lactones / Q000138:chemical synthesis; D018942:Macrolides; D013237:Stereoisomerism
D007783:Lactones; D018942:Macrolides; C119775:tedanolide