A nature-inspired Diels-Alder reaction facilitates construction of the bicyclo[2.2.2]octane core of andibenin B

A rapid synthesis of the bicyclo[2.2.2]octane core of andibenin B via a nature-inspired intramolecular [4+2] cycloaddition is described. This cycloaddition permits the construction of a sterically congested bicycle and simultaneously establishes three new all-carbon quaternary stereogenic centers in a highly efficient fashion. (C) 2009 Elsevier Ltd. All rights reserved.