Synthesis 2015; 47(17): 2599-2602
DOI: 10.1055/s-0034-1380684
paper
© Georg Thieme Verlag Stuttgart · New York

Direct, Biomimetic Synthesis of (+)-Artemone via a Stereoselective, Organocatalytic Cyclization

Eric D. Nacsa
Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, CA 91711, USA   Email: vosburg@hmc.edu
,
Brian C. Fielder
Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, CA 91711, USA   Email: vosburg@hmc.edu
,
Shannon P. Wetzler
Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, CA 91711, USA   Email: vosburg@hmc.edu
,
Veerasak Srisuknimit
Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, CA 91711, USA   Email: vosburg@hmc.edu
,
Jonathan P. Litz
Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, CA 91711, USA   Email: vosburg@hmc.edu
,
Mary J. Van Vleet
Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, CA 91711, USA   Email: vosburg@hmc.edu
,
Kim Quach
Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, CA 91711, USA   Email: vosburg@hmc.edu
,
David A. Vosburg*
Department of Chemistry, Harvey Mudd College, 301 Platt Boulevard, Claremont, CA 91711, USA   Email: vosburg@hmc.edu
› Author Affiliations
Further Information

Publication History

Received: 07 March 2015

Accepted after revision: 07 April 2015

Publication Date:
19 May 2015 (online)

Abstract

We present a four-step synthesis of (+)-artemone from (–)-linalool, featuring iminium organocatalysis of a doubly diastereoselective conjugate addition reaction. The strategy follows a proposed biosynthetic pathway, rapidly generates stereochemical complexity, uses no protecting groups, and minimizes redox manipulations.

Supporting Information

 
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