33628-85-2Relevant academic research and scientific papers
A SHORT SYTHESIS OF (+/-) 2-ACETYL-5,8-DIMETHOXY-1,2,3,4-TETRAHYDRO-2-NAPHTHOL. A KEY INTERMEDIATE FOR ANTHRACYCLINONE SYNTHSIS
Rao, Rama A. V.,Deshpande, V. H.,Reddy, Laxma N.
, p. 4373 - 4374 (1982)
Metal ammonia reduction of 2-acetyl-5,8-dimethoxynaphthalene gave 2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene which was converted to 2-acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol, a key intermediate for the synthesis of many antitumor anthracyclinones.
A NOVEL SYYNTHESIS OF (+/-)-2-ACETYL-5,8-DIMETHOXY-1,2,3,4-TETRAHYDRO-2-NAPHTHOL, A KEY INTERMEDIATE FOR THE SYNTHESIS OF ANTHRACYCLINONES
Terashima, Shiro,Tanno, Norihiko,Koga, Kenji
, p. 2749 - 2752 (1980)
The title compound ((+/-)-3) was prepared from readily available 5,8-dimethoxy-3,4-dihydro-2-naphthoic acid(4), according to the novel synthetic route visuelized in Scheme I.
Facile total syntheses of idarubicinone-7-β-D-glucuronide: Convenient preparations of AB-ring synthon using some carboxylic acid derivatives
Rho, Young S.,Park, Jihyung,Kim, Gyuil,Kim, Hyesun,Sin, Hongsig,Suh, Pyoung Won,Yoo, Dong Jin
, p. 1703 - 1722 (2007/10/03)
Regiospecific syntheses of idarubicinone coupled with D-glucuronic acid are described. Cyclization of dimethoxybenzene with carboxylic acid derivatives in polyphosphoric acid (PPA) in one step afforded the naphthalenones 7, which were transformed to the (
Total Synthesis of (+/-)-4-Demethoxydaunomycinone
Rao, A. V. Rama,Deshpande, V. H.,Sathaye, K. M.,Jaweed, S. M.
, p. 697 - 702 (2007/10/02)
2-Acetyl-5,8-dimethoxy-1,2,3,4-tetrahydro-2-naphthol (4), the key synthon for the total synthesis of various antitumor anthracyclinones, has been prepared either from 1,4-dimethoxynaphthalene and making use of metal-ammonia reduction or from benzoquinone and going through Diels-Alder reaction with 1,3-butadiene. 4 is then converted into (+/-)-4-demethoxydaunomycinone (3b).
Novel Synthesis of Optically Pure Anthracyclinone Intermediates by the Use of Microbial Asymmetric Reduction with Fermenting Baker's Yeast
Tamoto, Katsumi,Terashima, Shiro
, p. 4328 - 4339 (2007/10/02)
Microbial reduction of the racemic α-hydroxy ketones ((+/-)-3a,b) with fermenting baker's yeast was found to afford diastereomeric mixtures of the vicinal-diols ((-)-4a,b) and ((+)-5a,b) in 90 and 91percent yields, respectively.Separation of these diastereomers was readily accomplished by fractional recrystallization, giving pure (-)-4a,b and mixtures of (-)-4a,b and (+)-5a,b.Oxidation of these samples furnished optically pure anthracyclinone intermediates ((R)-(-)-3a,b) and their partially optically active antipodes ((S)-(+)-3a,b).The undesired enantiomers ((S)-(+)-3a,b) and vicinal-diols((+)-5a,b) could be recycled to (+/-)-3a,b and the prochiral ketones (6a,c) by racemization with p-toluenesulfonic acid and oxidative cleavage with sodium metaperiodate, respectively.Another important optically pure anthracyclinone intermediate ((R)-(-)-3c) was prepared from (R)-(-)-3a,b according to the reported method.Keywords - α-hydroxy ketone; microbial reduction; anthracycline; optically pure anthracyclinone; 4-demethoxyanthracycline; optically pure 4-demethoxyanthracyclinone; baker's yeast; oxidation; racemization; vicinal-diol
A NOVEL SYNTHESIS OF THE α-HYDROXYKETONE MOIETY OF ANTHRACYCLINONES BY THE USE OF 2-TRIMETHYLSILYLETHYNYLCERIUM(III) REAGENTS
Suzuki, Michiyo,Kimura, Yoshikazu,Terashima, Shiro
, p. 1543 - 1546 (2007/10/02)
2-trimethylsilylethynylcerium(III) reagents were found to efficiently react with 1,2,3,4-tetrahydronaphthalene-2-one derivatives, giving the corresponding adducts in high yields.Hydration of the adducts readily afforded the α-hydroxy methyl ketones which are versatile synthetic intermediates of natural and unnatural anthracyclinones.
A novel racemization mechanism for the α-hydroxy ketone moiety(C9-position) of optically active anthracyclinone derivatives
Terashima,Tamoto
, p. 2589 - 2592 (2007/10/02)
The facile acid-catalyzed racemization of optically active anthracyclinone derivatives((S)(+)-1a,b) was found to proceed through the ring-expanded seven-membered α-hydroxyketones(2 and/or 3 for (S)(+)-1a) by subjecting various plausible intermediates to t
