63542-40-5Relevant articles and documents
3,5-dihydroxy-4-trifluoromethoxybenzyl alcohol (3,5-dihydro x y-4-metho x ybenzylalcohol) synthesis method (by machine translation)
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Paragraph 0029-0037, (2017/04/11)
PROBLEM TO BE SOLVED: earpick not derived from a so-called new antioxidant and anti-oxidant composition 3,5-dihydroxy-4-efficient trifluoromethoxybenzyl alcohol, to provide a method for synthesizing high purity. SOLUTION: subgallate dimethyl formamide suc
Biomimetic synthesis of (±)-galanthamine and asymmetric synthesis of (-)-galanthamine using remote asymmetric induction
Node, Manabu,Kodama, Sumiaki,Hamashima, Yoshio,Katoh, Takahiro,Nishide, Kiyoharu,Kajimoto, Tetsuya
, p. 1662 - 1679 (2007/10/03)
(±)-Galanthamine (1) was synthesized in excellent yield by applying PIFA-mediated oxidative phenol coupling of N-(4-hydroxy)phenethyl-N-(3′, 4′,5′-trialkoxy)benzyl formamide (15b) as a key step. Because of the symmetrical characteristics of the pyrogallol moiety in the substrate (15b), the phenol coupling resulted in a sole coupling product except for volatile components from the oxidizing agent. On the basis of the successful results of the above strategy, (-)-galanthamine (1) was synthesized by employing a novel remote asymmetric induction, where conformation of the seven-membered ring in the product of the phenol coupling was restricted by forming a fused-chiral imidazolidinone ring with D-phenylalanine on the benzylic C-N bond of the tri-O-alkylated gallyl amino moiety. The conformational restriction and successive debenzylation of the protected hydroxyl groups on the pyrogallol ring caused diastereoselective cyclization to yield a cyclic ether having the desired stereochemistry for the synthesis of (-)-1.
