Enantioselective intramolecular Friedel-Crafts-type alpha-arylation of aldehydes.
Enantioselective organo-SOMO catalysis has, in the last two years, been the subject of considerable development and exploration. A number of new and unique transformations have been reported, such as alpha-allylation, alpha-oxyamination, alpha-enolation, and alpha-vinylation of aldehydes. Herein, we report a modification of this activation mode that involves the intramolecular Friedel-Crafts-type alpha-arylation of aldehydes carrying electron-donating groups on their aromatic nucleus and its application to the total synthesis of demethyl calamenene, a potent cytotoxic agent against human adenocarcinoma A 549.
Nicolaou
K C
KC
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute,10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Reingruber
Rüdiger
R
Sarlah
David
D
Bräse
Stefan
S
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000138:chemical synthesis; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D003500:Cyclization; D000081223:Polycyclic Sesquiterpenes; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis*
D000447:Aldehydes; D000970:Antineoplastic Agents; D001643:Bridged Bicyclo Compounds; D000081223:Polycyclic Sesquiterpenes; D013729:Terpenes; C502644:calamenene