88391-16-6

Basic information

• Product Name: (+/-)-Aklavinon-I
• CAS NO: 88391-16-6
• Molecular Weight: 412.396
• Mol File: 88391-16-6.mol

Chemical Properties

• CAS DataBase Reference: (+/-)-Aklavinon-I(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-Aklavinon-I(88391-16-6)
• EPA Substance Registry System: (+/-)-Aklavinon-I(88391-16-6)

Safety Data

• Hazardous Substances Data: 88391-16-6(Hazardous Substances Data)

Upstream product

• 78773-10-1 4-Bromo-2-ethyl-2,5,7-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester 
• 88365-17-7 9,10-Dihydro-4-hydroxy-5-methoxy-9,10-dioxo-3-(3-oxopentyl)-2-anthracenessigsaeure-methylester 
• 80173-04-2 methyl(9-RS,10-SR)-9-ethyl-6,9-dihydroxy-4-methoxy-5,12-dioxo-5,7,8,9,10,12-hexahydronaphthacene-10-carboxylate 
• 78773-17-8 9-epi-aklavinone 7-methyl ether 
• 19260-55-0 t-2-Ethyl-1,2,3,4,6,11-hexahydro-c-2,5,7-trihydroxy-6,11-dioxo-r-1-naphthacencarbonsaeuremethylester 
• 77825-05-9 3-Brommethyl-1-(2,2-dimethylpropionyloxy)-8-methoxy-2-(3-oxopentyl)-9,10-anthrachinon 
• 80173-04-2 c-2-Ethyl-1,2,3,4,6,11-hexahydro-t-2,5-dihydroxy-7-methoxy-6,11-dioxo-r-1-naphthacencarbonsaeure-methylester 
• 82247-61-8 10-(R,S)-carbomethoxy-6-ethoxy-9(R,S)-ethyl-9(R,S)-hydroxy-4-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione 
• 82247-63-0 10-(R,S)-carbomethoxy-6-ethoxy-9(S,R)-ethyl-9(S,R)-hydroxy-4-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione 
• 78773-17-8 aklavinone 7-methyl ether 
• 78773-17-8 7-epi-aklavinone 7-methyl ether 
• 78821-96-2 methyl 9(R,S)-ethyl-4,6,9(R,S)-trihydroxy-5,12-dioxo-7,8,9,10-tetrahydronaphthacene-10(R,S)-carboxylate 
• 88365-16-6 3-(2-Diazo-acetyl)-1-hydroxy-8-methoxy-2-(3-oxo-pentyl)-anthraquinone 
• 88365-13-3 9,10-Dihydro-4-hydroxy-5-methoxy-9,10-dioxo-3-(3-oxopentyl)-2-anthracencarbonsaeure 

Downstream Products

• 65222-75-5 (1S,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-((2R,4S,5S,6S)-5-hydroxy-6-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester 
• 65222-75-5 N-demethylaklavin 
• 78773-24-7 (1R,2R,4S)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester 
• 78773-24-7 (1S,2S,4R)-2-Ethyl-2,5,7-trihydroxy-4-[(2R,4S,5S,6S)-6-methyl-4-[methyl-(2,2,2-trifluoro-acetyl)-amino]-5-(4-nitro-benzoyloxy)-tetrahydro-pyran-2-yloxy]-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacene-1-carboxylic acid methyl ester 
• 60504-57-6 aklavin 
• 16234-96-1 (+)-aklavinone 

Relevant articles and documents

1(4H)-Naphthalenones in Anthracyclinone Synthesis: A New Route for the Total Synthesis of (+/-)-Aklavinone

A brief route for total synthesis of (+/-)-aklavinone (1a), the aglycon of the anticancer antibiotic aclacinomycin (1b), is described.Key features of the synthesis are the development of a brief, efficient route to the 1(4H)-naphthalenone 11, which was used as a synthon for the A and B rings, and homologation of keto aldehyde 17 to the keto anthraquinone acetic ester 16 via the intermediacy of the ketene thioacetal 19.

SYNTHESES OF (+/-)-AKLAVINONES. APPLICATION OF THE STEREOCONTROLLED "ZIPPER" BICYCLO-CYCLIZATION REACTION

Efficient syntheses of (+/-)-aklavinones; (+/-)-aklavinone (1), (+/-)-auramycinone (2), and (+/-)-13-methylaklavinone (3), are described.A key process of the tetracyclic ring construction in these syntheses is a stereocontrolled "zipper" bicyclo-cyclizati

A FACILE TOTAL SYNTHESIS OF RACEMIC AKLAVINONE

A convergent total synthesis of aklavinone, based on the annelation reaction of cyanophthalide addition to an enone as the key step, was accomplished.

An Efficient Total Synthesis of (+/-)-Aklavinone

An 11-step total synthesis of (+/-)-aklavinone from 1,3-cyclohexadione is reported.The key steps include a Diels-Alder condensation of 3 and 4 and the stereoselective aldol condensation of 21 to 22.The overall yield is ca. 13percent.