Enantioselective total synthesis of the oral contraceptive desogestrel by a double Heck reaction.
A novel enantioselective total synthesis of the oral contraceptive desogestrel (2) is described, in which the tetracyclic steroid core is formed by a sequence of two consecutive Heck reactions. Conversion of the known enantiopure diketone 7 led to the chiral bicycle 6 which was used for a diastereoselective intermolecular Heck reaction with vinyliodide 5 to give 15. In the following intramolecular Heck reaction, the tetracyclic ring system was formed to give 4, from which the synthesis of desogestrel (2) was furnished.
Tietze
Lutz F
LF
Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, Göttingen, Germany. ltietze@gwdg.de
Krimmelbein
Ilga K
IK
D002384:Catalysis; D003280:Contraceptives, Oral, Synthetic / Q000138:chemical synthesis*; D017135:Desogestrel / Q000138:chemical synthesis*; D006844:Hydrocarbons, Cyclic / Q000737:chemistry; D006847:Hydrocarbons, Iodinated / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D008956:Models, Chemical; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
D003280:Contraceptives, Oral, Synthetic; D006844:Hydrocarbons, Cyclic; D006847:Hydrocarbons, Iodinated; D007659:Ketones; D014753:Vinyl Compounds; D010165:Palladium; D017135:Desogestrel