Anomalous transformation of tricyclo[3.3.0.02,8]octan-3-ones into bicyclo[3.2.1]octan-3-ones, a novel route to (±)-quadrone
Abstract
A novel route to (±)-quadrone (5) has been developed via an anomalous C(1)–C(2) bond cleavage of 4-benzyloxymethyl-7,7-dimethyl-3-oxotricyclo[3.3.0.02,8]octane-5- acetic acid (11) by an intramolecular participation of the carboxy group.