Total synthesis of (-)-cleistenolide.
The first total synthesis of Cleistenolide, a novel natural product recently isolated from the Annonaceae species Cleistochlamys kirkii Oliver, is described. The synthesis proceeds in six steps and 18% overall yield, starting from an enantiopure C2-symmetric building block and using a Sharpless epoxidation, a selective epoxide opening, and a ring-closing metathesis reaction.
Schmidt
Bernd
B
Institut fuer Chemie, Organische Synthesechemie, Universitaet Potsdam, Karl-Liebknecht-Strasse 24-25, D-14476 Golm, Germany. bernd.schmidt@uni-potsdam.de
Kunz
Oliver
O
Biernat
Anne
A
D029061:Annonaceae / Q000737:chemistry; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D004852:Epoxy Compounds; D011753:Pyrones; C550131:cleistenolide