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

Kanny K. Wan; Corwyn D. Evans-Klock; Brian C. Fielder; David A. Vosburg

doi:10.1055/s-0033-1338429

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(11): 1541-1545
DOI: 10.1055/s-0033-1338429

paper

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

Kanny K. Wan

Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, CA 91711, USA Fax: +1(909)6077577 eMail: vosburg@hmc.edu

,

Corwyn D. Evans-Klock

Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, CA 91711, USA Fax: +1(909)6077577 eMail: vosburg@hmc.edu

,

Brian C. Fielder

Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, CA 91711, USA Fax: +1(909)6077577 eMail: vosburg@hmc.edu

,

David A. Vosburg*

Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, CA 91711, USA Fax: +1(909)6077577 eMail: vosburg@hmc.edu

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Abstract

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This paper is dedicated to Prof. Christopher T. Walsh on the occasion of his retirement in 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.

Key words

davanone - terpenoids - total synthesis - stereoselective synthesis - green chemistry - asymmetric allylic O-alkylation

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Referenzen

References
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