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.
© 2013 Georg Thieme Verlag KG
“Synthesis of cis and trans davanoids: Artemone, hydroxydavanone, isodavanone, and nordavanone,” Wan, K.K.; Evans-Klock, C.D.; Fielder, B.C.; Vosburg, D.A. Synthesis 2013, 45, 1541-1545. doi: 10.1055/s-0033-1338429