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.
Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, Göttingen, Germany. ltietze@gwdg.de
Lutz F
LF
Tietze
Ilga K
IK
Krimmelbein
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