ChemInform Abstract: ANTHRACYCLINES. X. THE ENANTIOSPECIFIC SYNTHESIS OF (-)-(7R)-7-ACETYL-7-HYDROXY-4,4-DIMETHOXY-5,6,7,8-TETRAHYDRONAPHTHALEN-1(4H)-ONE; A TYPE I CHIRAL DIENONE FOR THE SYNTHESIS OF 7-DEOXYDAUNOMYCINONE

Autor:	Richard A. Russell, Ronald N. Warrener, R. W. Irvine, P. S. Gee
Rok vydání:	1985
Předmět:	chemistry.chemical_classification chemistry.chemical_element Tributyltin hydride General Medicine Medicinal chemistry 7-deoxydaunomycinone chemistry.chemical_compound chemistry Amide Thallium Phenol Methyllithium Lactone Catalytic hydrogenation
Zdroj:	Chemischer Informationsdienst. 16
ISSN:	0009-2975
DOI:	10.1002/chin.198505190
Popis:	8-Benzyloxy-5-methoxy-3,4-dihydronaphthalene-2-carboxylic acid (34) has been prepared by a four-step sequence from 5-methoxy-8-hydroxy-3,4-dihydronaphthalen-1(2H)-one. Condensation of the unsaturated acid (34) with ethyl (S)-prolinate in the presence of dicyclohexylcarbodiimide afforded the amide (35) which was enantioselectively cyclized to the bromo lactone (37). Debromination with tributyltin hydride and subsequent reaction of the lactone with methyllithium afforded (-)-(2R)-2-acetyl-8-benzyloxy-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-ol. Removal of the benzyl ether by catalytic hydrogenation and oxidation of the resulting phenol with thallium(III) nitrate afforded the title chiral dienone.
Databáze:	OpenAIRE
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