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

Authors

Kanny K. Wan '11, Harvey Mudd College
Corwyn D. Evans-Klock '13, Harvey Mudd College
Brian C. Fielder '14, Harvey Mudd College
David A. Vosburg, Harvey Mudd CollegeFollow

Student Co-author

HMC Undergraduate

Document Type

Article

Department

Chemistry (HMC)

Publication Date

2013

Abstract

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.

Rights Information

© 2013 Georg Thieme Verlag KG

DOI

10.1055/s-0033-1338429

Recommended Citation

“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