347359-71-1Relevant articles and documents
α,β-Dibenzyl-γ-butyrolactone lignan alcohols: total sytnhesis of (+/-)-7'-hydroxyenterolactone, (+/-)-7'-hydroxymatairesinol and (+/-)-8-hydroxyenterolactone
Maekelae, Taru H.,Kaltia, Seppo A.,Waehaelae, Kristiina T.,Hase, Tapio A.
, p. 777 - 784 (2001)
Two trans-α,β-dibenzyl-γ-butyrolactone lignans carrying a hydroxyl group at the β-benzylic carbon aton and a α-hydroxy α,β-dibenzyl-γ-butyrolactone lignan were synthesized in racemic form using the tandem conjugate addition reaction to construct the basic lignan skeleton. Subsequent reaction steps involved either a catalytic reduction of the regenerted keto group to the alcohol, or a hydrogenolysis to benzylic methylene followed by lactone enolate formation and oxidation to give the α-hydroxybutyrolactones. These procedures were applied for the synthesis of 7'-hydroxyenterolactones and 7'-hydroxymatairesinols, and 8-hydroxyenterolacotones, respectively. The diastereomeric mixtures of these compounds were separated either by HPLC techniques or column chromatography and the structures were elucidated using NMR spectroscopy.
Convenient preparation and spectroscopic characterization of 7r-hydroxymatairesinol
Ciriello, Umberto,Colombo, Eleonora,Paladino, Giuseppe,Passarella, Daniele
, (2021/09/30)
The preparation of 7R-HMR (allo-hydroxymatairesinol) is reported by: (a) NaBH4 kinetic reduction of 7R/7S diastereomeric mixture; and (b) epimerization of the C7 hydroxyl group by Mitsunobu reaction and subsequent ester hydrolysis. The availability of highly pure target compound (7R-HMR) made it possible to confirm the structure of the target compound and to complete the full spectroscopic characterization.
Asymmetric aldol approach to dibenzylbutyrolactone lignans: Synthesis of (-)-(7′S)-hydroxymatairesinol and (-)-(7′S)-hydroxyarctigenin
Hajra, Saumen,Mandal, Abhisek,Hazra, Sunit
supporting information, p. 2171 - 2173 (2013/05/08)
A competent and general asymmetric synthesis of 7′- hydroxydibenzylbutyrolactone lignans such as (7′S)-hydroxymatairesinol and (7′S)-hydroxyarctigenin has been reported from N-succinyl-2-oxazolidinone in six steps where diastereoselective aldol reaction and stereoselective alkylation serve as the key steps.