139006-77-2Relevant academic research and scientific papers
Divergent Total Syntheses of Gymnothelignan N, Beilschmin A, and Eupomatilones 1, 3, 4, and 7
Choi, Hosam,Choi, Joohee,Han, Jongyeol,Lee, Kiyoun
, p. 4316 - 4322 (2022/03/15)
A seven-step asymmetric total synthesis of gymnothelignan N is detailed in the current report. The approach is based on an early-stage one-carbon homologative lactonization reaction, which we recently revisited and modified to construct the core γ-butyrolactone motif with the requisite β,γ-vicinal stereogenic centers. By design, the utilization of the same chiral γ-butyrolactone intermediate permitted the rapid and effective divergent assembly of optically active eupomatilones 1, 3, 4, and 7 in five or six steps from commercially available materials. This represents one of the shortest and highest-yielding syntheses reported to date.
Dynamic kinetic resolution of α,β-unsaturated lactones through asymmetric copper-catalyzed conjugate reduction: Application to the total synthesis of eupomatilone-3
Rainka, Matthew P.,Milne, Jacqueline E.,Buchwald, Stephen L.
, p. 6177 - 6180 (2007/10/03)
(Chemical Equation Presented) Only six steps were needed for the total synthesis of eupomatilone-3 in 48 % overall yield thanks to the development of a dynamic kinetic resolution that allowed the reductive conversion of a racemic α,β-unsaturated butenolid
