Asymmetric synthesis of a tricyclic benzofuran motif: a privileged core structure in biologically active molecules.
Journal article, 2010

An efficient synthetic strategy for the asymmetric synthesis of a hexahydrodibenzofuran core structure, with a quaternary stereogenic center, emerges by employing a chiral reduction using Corey's (S)-Me-CBS-oxazaborolidine reagent followed by a Mitsunobu reaction to set the stereochemistry. A Pd-mediated intramolecular Heck reaction concludes the tricyclic core structure. Finally, a Pd/C catalyzed reduction yields the target molecule in 21% overall yield over 6 steps.

Author

Henrik Sundén

University of Gothenburg

Roger Olsson

University of Gothenburg

Organic and Biomolecular Chemistry

1477-0520 (ISSN) 1477-0539 (eISSN)

Vol. 8 4831-3

Subject Categories

Chemical Sciences

DOI

10.1039/c0ob00331j

PubMed

20835457