Two-step, Stereoselective Synthesis of Linalyl Oxides by Asymmetric Allylic O-alkylation

Each of the four tetrahydrofuran linalyl oxides was prepared by a Sharpless asymmetric dihydroxylation of geranyl acetate with AD-mix-α or AD-mix-β, followed by a stereoselective palladium-mediated cyclization using the chiral ligand C3-TunePhos

Synthesis of cis- and trans-Davanoids: Artemone, Hydroxydavanone, Isodavanone, and Nordavanone

A concise and versatile synthesis of both cis and trans dia­stereomers of the natural products artemone, hydroxydavanone, isodavanone, and nordavanone has been accomplished. The preparation of trans-davanone is also described. Each synthesis is six to eight steps from geranyl acetate, with differentiation between cis and trans products occurring through a diastereoselective cyclization prior to derivatization. Many of these compounds are minor components of davana oil and have now been synthesized for the first time