Total synthesis of (±)-(1β,4β,4aβ,8aα)-4,8a-dimethyl-octahydro-naphthalene-1,4a(2 H )-diol

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The first total synthesis of (±)-(1β,4β,4aβ,8aα)-4,8a-dimethylocta-hydronaphthalene-1,4a(2 H )-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 ).