The first total synthesis of (+/-)-methyl gummiferolate (Ib) has been achieved with a high diastereoselectivity. The key steps included the homoallyl-homoallyl radical rearrangement reaction of the enyne 8 to afford the suitably functionalized bicyclo[2.2.2]octane 9 and the intramolecular Diels-Alder reaction of the tetraene 12 for the construction of the AB ring system of Ib.