Direct, biomimetic synthesis of (+)-artemone via a stereoselective, organocatalytic cyclization

Authors

Eric D. Nacsa, Columbia University
Brian C. Fielder
Shannon P. Wetzler, Harvey Mudd College
Veerasak Srisuknimit, Harvard University
Jonathan P. Litz, University of Washington
Mary J. Van Vleet, University of Wisconsin-Madison
Kim Quach, Yale University
David A. Vosburg, Harvey Mudd CollegeFollow

Document Type

Article

Department

Chemistry (HMC)

Publication Date

Spring 5-19-2015

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.

Rights Information

© 2015, Thieme

Recommended Citation

Direct, biomimetic synthesis of (+)-artemone via a stereoselective, organocatalytic cyclization,” Nacsa, E.D.; Fielder, B.C.; Wetzler, S.P.; Srisuknimit, V.; Litz, J.P.; Van Vleet, M.J.; Quach, K.; Vosburg, D.A. Synthesis 2015