The first total synthesis of (±)-(1β,4β,4aβ,8aα)-4,8a-dimethylocta-hydronaphthalene-1,4a(2H)-diol (1), a degraded sesquiterpene isolated from a fermentation broth of Streptomyces albolongus, has been achieved via three different synthetic approaches (13–15 steps) starting from racemic Wieland–Miescher ketone (2). The configuration of hydroxyl groups at C-1 and C-4a in 1 was availably managed using the Mitsunobu reaction and stereo- and regioselective epoxidation. Moreover, the syntheses of configuration isomers 12, 17, 45 and 54 were also described in the present study.