- SIMPLE SYNTHESIS OF 2-ACETYL-5,8-DIMETHOXY-3,4-DIHYDRONAPHTHALENE, A KEY INTERMEDIATE FOR THE SYNTHESIS OF OPTICALLY ACTIVE ANTHRACYCLIONES
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2-Acetyl-5,8-dimethoxy-3,4-dihydronaphthalene is synthesised easily, starting from 2-acetyl-5,8-dimethoxytetralone.
- Rao, A. V. Rama,Deshpande, V. H.,Rao, B. Ramamohan,Ravichandran, K.
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- Simple synthesis of 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene: A key intermediate for the synthesis of 4-demethoxydaunomycinone
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2-Acetyl-5,8-dimethoxy-3,4-dihydronaphthalene is prepared by using a 1,3-dipolar cycloaddition of nitrile oxide to the corresponding dihydronaphthalene.
- Chavan, Subhash P.,Subbarao, Y. Tripura,Gopal, Chittiboyina Amar
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- Efficient enantioselective synthesis of (R)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, the key intermediate in the synthesis of anthracycline antibiotics
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A simple, efficient, enantioselective synthesis of (R)-2-acetyl-2-hydroxy-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene, the key intermediate in the synthesis of anthracycline antibiotics, is described. The synthetic procedure starts with the Sharpless asymmetric dihydroxylation of 2-acetyl-5,8-dimethoxy-3,4-dihydronaphthalene: the diol obtained is regioselectively transformed into the corresponding chloroacetate which is dehalogenated and saponified to give the desired title compound in four steps with satisfactory yield (52%). No separation step is necessary at any point of the synthetic process. An efficient procedure for the synthesis of the starting enone and the stereoselectivity of the methanolysis of the intermediate chloroacetate are also reported.
- Badalassi, Fabrizio,Crotti, Paolo,Di Bugno, Cristina,D'Arata, Fabio,Favero, Lucilla,Ramacciotti, Alessio
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p. 3155 - 3161
(2007/10/03)
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- Total Synthesis of (+/-)-4-Demethoxydaunomycinone
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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).
- Rao, A. V. Rama,Deshpande, V. H.,Sathaye, K. M.,Jaweed, S. M.
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p. 697 - 702
(2007/10/02)
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- A HIGH YIELD SYNTHESIS OF (+/-)-5,8-DIMETHOXY-2-α-HYDROXYETHYL-3,4-DIHYDRONAPHTHALENE, A KEY INTERMEDIATE IN ANTRACYCLINONE SYNTHESIS
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The dimethoxytetralol (2) gives on Vilsmeier reaction the dihydronaphthaldehyde (3) (yield, 92percent), which on Grignard reaction with MeMgI affords the title compound (6) (yield, ca. 100percent), the reactions constituting a high yield synthesis of this important antracyclinone intermediate.
- Reddy, M. Parameswara,Rao, G. S. Krishna
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p. 3549 - 3550
(2007/10/02)
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- A NOVEL SYYNTHESIS OF (+/-)-2-ACETYL-5,8-DIMETHOXY-1,2,3,4-TETRAHYDRO-2-NAPHTHOL, A KEY INTERMEDIATE FOR THE SYNTHESIS OF ANTHRACYCLINONES
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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.
- Terashima, Shiro,Tanno, Norihiko,Koga, Kenji
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p. 2749 - 2752
(2007/10/02)
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- 4-DEMETHOXY-9-DEOXY-9-METHYLDAUNORUBICIN
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The synthesis of the α-daunosaminyl derivatives of (+)- and (-)-4-demethoxy-9-deoxy-9-methyldaunomycinone is reported.The new compounds are inactive in the P 388 lymphocytic leukemia test.
- Giardino, Pietro,Vigevani, Aristide,Bernardi, Luigi,Arcamone, Federico
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p. 101 - 104
(2007/10/02)
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