Total Synthesis of ent-lepadin F and G by a tandem ene-yne-ene ring closing metathesis.
The first total synthesis of the decahydroquinoline-alkaloids lepadin F and G is described. As key steps, the decahydroquinoline skeleton has been synthesized by utilizing a tandem ene-yne-ene ring closing metathesis of an acyclic precursor followed by a stereoselective hydrogenation of the resulting diene moiety. The selectivity of these two steps was achieved by a well-directed hydroxyl protection strategy. The synthesized compounds were found to be enantiomers of natural lepadin F and G, consequently the absolute configuration of the natural compounds could be assigned.
Niethe
Alexander
A
Institut für Chemie, Technische Universität Berlin, Strasse des 17. Juni 135, D-10623 Berlin, Germany.
Fischer
Dirk
D
Blechert
Siegfried
S
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D006873:Hydroquinones / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D014961:X-Ray Diffraction
D000470:Alkaloids; D006873:Hydroquinones; D011804:Quinolines; C455162:lepadin F; C455163:lepadin G; C031927:hydroquinone