Enantioselective intramolecular Friedel-Crafts-type alpha-arylation of aldehydes.

Abstract

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.

• Authors: K C Nicolaou, Rüdiger Reingruber, David Sarlah, Stefan Bräse
• Journal: Journal of the American Chemical Society (J Am Chem Soc) Vol. 131 Issue 6 Pg. 2086-7 (Feb 18 2009) ISSN: 1520-5126 [Electronic] United States
• PMID: 19173649 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Research Support, U.S. Gov't, Non-P.H.S.)

Chemical References

• Aldehydes
• Antineoplastic Agents
• Bridged Bicyclo Compounds
• Polycyclic Sesquiterpenes
• Terpenes
• calamenene

Topics

• Aldehydes (chemical synthesis, chemistry)
• Antineoplastic Agents (chemical synthesis)
• Bridged Bicyclo Compounds (chemical synthesis)
• Crystallography, X-Ray
• Cyclization
• Polycyclic Sesquiterpenes
• Stereoisomerism
• Terpenes (chemical synthesis)