89067-58-3Relevant articles and documents
The first synthesis of (±)-cycloolivil: A highly stereoselective synthesis of 3-hydroxy-1-aryltetralin lignans based on the stereoselective hydroxylation of α,β-dibenzyl-γ-butyrolactones
Moritani,Ukita,Ohmizu,Iwasaki
, p. 671 - 672 (1995)
Cycloolivil, a representative example of 3-hydroxy-1-aryltetralin lignans, was stereoselectively synthesised in good yields based on the stereoselective electrophilic addition to the metal enolate of α,β-disubstituted γ-butyrolactone as a key step.
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 (2007/10/03)
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.
A highly stereoselective synthesis of 3-hydroxy-1-aryltetralin lignans based on the stereoselective hydroxylation of α,β-dibenzyl-γ-butyrolactones: the first synthesis of (+/-)-cycloolivil
Moritani, Yasunori,Ukita, Tatsuzo,Hiramatsu, Hajime,Okamura, Kimio,Ohmizu, Hiroshi,Iwasaki, Tameo
, p. 2747 - 2754 (2007/10/03)
Lignans of the 3-hydroxy-1-aryltetralin series 1 and 2 have been synthesised in good yields in a highly diastereoselective manner.The stereochemistry at C-1, C-2 and C-3 of 1 and 2 was completely controlled by an electrophilic addition of oxodiperoxymolyb
ETUDES DE LIGNANES 7 - SYNTHESES TOTALES DES (+-)-α ET -β-CONIDENDRINES ET DES METHYL (+-)-α ET -β-CONIDENDRALS
Dhal, Robert,Nabi, Yahia,Brown, Eric
, p. 2005 - 2016 (2007/10/02)
Michael addition of the carbanion of the dithian 8 on butenolide, followed by alkylation with the benzylic bromide 11 and regeneration of the ketonic carbonyl group, gave the α,β-disubstituted lactone 13.Reduction of the ketonic carbonyl of the latter usi
SYNTHESE TOTALE DE LA (d,l) α-CONIDENDRINE
Nabi, Yahia,Dhal, Robert,Brown, Eric
, p. 1543 - 1546 (2007/10/02)
Michael addition of the carbanion of the dithian 7 (derived from O-benzylvanillin) on butenolide, afforded the saturated lactone 8.Alkylation of the latter with the benzylic bromide 6, followed by regeneration of the carbonyl group gave the α,β-disubstituted lactone 10.Reduction of the ketonic carbonyl group of compound 10 using NaBH4, followed by treatment with CF3CO2H and catalytic hydrogenolysis afforded (d,l)α-conidendrin 1.
