Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 8, Issue 21, Pages 4831-4833Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob00331j
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- Michael J. Fox foundation
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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.
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