Issue 21, 2010

Asymmetric synthesis of a tricyclic benzofuran motif: a privileged core structure in biologically active molecules

Abstract

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.

Graphical abstract: Asymmetric synthesis of a tricyclic benzofuran motif: a privileged core structure in biologically active molecules

Supplementary files

Article information

Article type
Communication
Submitted
28 Jun 2010
Accepted
18 Aug 2010
First published
08 Sep 2010

Org. Biomol. Chem., 2010,8, 4831-4833

Asymmetric synthesis of a tricyclic benzofuran motif: a privileged core structure in biologically active molecules

H. Sundén and R. Olsson, Org. Biomol. Chem., 2010, 8, 4831 DOI: 10.1039/C0OB00331J

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