30925-48-5Relevant academic research and scientific papers
Direct, Biomimetic Synthesis of (+)-Artemone via a Stereoselective, Organocatalytic Cyclization
Nacsa, Eric D.,Fielder, Brian C.,Wetzler, Shannon P.,Srisuknimit, Veerasak,Litz, Jonathan P.,Van Vleet, Mary J.,Quach, Kim,Vosburg, David A.
, p. 2599 - 2602 (2015/09/01)
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. Georg Thieme Verlag Stuttgart.
Synthesis of cis- and trans -davanoids: Artemone, hydroxydavanone, isodavanone, and nordavanone
Wan, Kanny K.,Evans-Klock, Corwyn D.,Fielder, Brian C.,Vosburg, David A.
, p. 1541 - 1545 (2013/07/19)
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. Georg Thieme Verlag Stuttgart New York.
Stereoselective Syntheses of (+)-Davanone and (+)-Artemone via Anti-selective Epoxidation and Iodo-cyclization
Honda, Yutaka,Ori, Aiichiro,Tsuchihashi, Gen-ichi
, p. 1259 - 1262 (2007/10/02)
Chiral sesquiterpenes, (+)-Davanone and (+)-Artemone, were synthesized via anti-selective epoxidation and iodo-cyclization by the use of (S)-ethyl lactate as a chiral source.
