A total synthesis of (±)-1-desoxyhypnophilin: using ring closing metathesis for the construction of cyclic enones

The paper describes the first total synthesis of (±)-1-desoxyhypnophilin, a linear triquinane isolated from the East African mushroom Lentinus crinitus which displays promising antimicrobial activity. The key strategic feature is a new cyclopentannulation method for appending cycloalkenones onto ketones involving sequential use of a ring closing metathesis reaction with a tertiary allylic alcohol and a PCC induced oxidative rearrangement.