165606-47-3Relevant academic research and scientific papers
Enantioselective biomimetic total syntheses of kuwanons i and J and brosimones A and B
Han, Jianguang,Li, Xia,Guan, Yong,Zhao, Wenjun,Wulff, William D.,Lei, Xiaoguang
, p. 9257 - 9261,5 (2014)
The first enantioselective total syntheses of prenylflavonoid Diels-Alder natural products (-)-kuwanonI, (+)-kuwanonJ, (-)-brosimoneA, and (-)-brosimoneB have been accomplished from a common intermediate based on a concise synthetic strategy. Key elements of the synthesis include a biosynthesis-inspired asymmetric Diels-Alder cycloaddition mediated by a chiral ligand/boron Lewis acid, as well as a process involving regioselective Schenck ene reaction, reduction, and dehydration to realize a biomimetic dehydrogenation for generation of the required diene precursor. Furthermore, a remarkable tandem inter-/intramolecular asymmetric Diels-Alder cycloaddition process was applied for the synthesis of (-)-brosimoneA. Four in a row: The first enantioselective total syntheses of the prenylflavonoid natural products (-)-kuwanonI, (+)-kuwanonJ, (-)-brosimoneA, and (-)-brosimoneB have been accomplished based on a concise synthetic strategy. Key elements of the synthesis include a biosynthesis-inspired asymmetric Diels-Alder cycloaddition mediated by a chiral ligand/boron Lewis acid, as well as a process involving regioselective Schenck ene reaction, reduction, and dehydration.
