136805-24-8Relevant academic research and scientific papers
High-yield total synthesis of (-)-strictinin through intramolecular coupling of gallates
Michihata, Naoki,Kaneko, Yuki,Kasai, Yusuke,Tanigawa, Kotaro,Hirokane, Tsukasa,Higasa, Sho,Yamada, Hidetoshi
, p. 4319 - 4328 (2013)
This paper describes a total synthesis of (-)-strictinin, an ellagitannin that is 1-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl (HHDP)-β-d-glucose. In the study, total efficiency of the synthesis was improved to produce a 78% overall yield in 13 steps from d-glucose. In the synthesis, formation of the 4,6-(S)-HHDP bridge including the 11-membered bislactone ring was a key step, in which intramolecular aryl-aryl coupling was adopted. The coupling was oxidatively induced by CuCl2-n-BuNH2 with perfect control of the axial chirality, and the reaction conditions of this coupling were optimized thoroughly to achieve the quantitative formation of the bridge.
Studies on the Synthesis of Aryl Ethers Using Arene-Manganese Chemistry
Pearson, Anthony J.,Bruhn, Paul R.
, p. 7092 - 7097 (2007/10/02)
Selective arylation of polyfunctional phenols, using chlorobenzene- and p-chlorotoluene-manganese tricarbonyl cations, is described.The intermediate arene-manganese complexes are found to undergo stereo- and regioselective reactions with Schoellkopf's chiral glycine enolate equivalent to give dienyl-Mn(CO)3 complexes.Treatment of these complexes with N-bromosuccinimide at room temperature, followed by hydrolysis of the dihydropyrazine, gives diaryl ethers in which one of the aromatic rings is an arylglycine methyl ester.
