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Issue 21, 2010
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Asymmetric synthesis of a tricyclic benzofuran motif: a privileged core structure in biologically active molecules

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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

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Supplementary files

Article information


Submitted
28 Jun 2010
Accepted
18 Aug 2010
First published
08 Sep 2010

Org. Biomol. Chem., 2010,8, 4831-4833
Article type
Communication

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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