28399-50-0

Basic information

• Product Name: rabelomycin
• Synonyms: rabelomycin;(-)-3,4-Dihydro-3,6,8-trihydroxy-3-methylbenz[a]anthracene-1,7,12(2H)-trione
• CAS NO: 28399-50-0
• Molecular Formula: C19H14O6
• Molecular Weight: 0
• Mol File: 28399-50-0.mol

Chemical Properties

• Boiling Point: 675.7°Cat760mmHg
• Flash Point: 376.4°C
• Appearance: /
• Density: 1.576g/cm³
• Vapor Pressure: 3.52E-19mmHg at 25°C
• Refractive Index: 1.728
• CAS DataBase Reference: rabelomycin(CAS DataBase Reference)
• NIST Chemistry Reference: rabelomycin(28399-50-0)
• EPA Substance Registry System: rabelomycin(28399-50-0)

Safety Data

• Hazardous Substances Data: 28399-50-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H14O6/c1-19(25)6-8-5-11(21)15-16(13(8)12(22)7-19)17(23)9-3-2-4-10(20)14(9)18(15)24/h2-5,20-21,25H,6-7H2,1H3/t19-/m1/s1

Upstream product

• 155652-46-3 rac-1-deoxyrabelomycin 
• 155652-39-4 3-Methyl-3-(1,1,2,2,2-pentamethyl-disilanyl)-cyclohexanone 
• 155652-41-8 ethyl (E/Z)-<3-methyl-3-(pentamethyldisilanyl)cyclohexylidene>acetate 
• 155652-45-2 1,2,3,4-tetrahydro-6,8-dihydroxy-3-methyl-3-(hydroxydimethylsilanyl)benzoanthracen-7,12-dione 
• 155652-44-1 6-ethoxy-1,2,3,4-tetrahydro-8-hydroxy-3-methyl-3-(pentamethyldisilanyl)benzoanthracen-7,12-dione 
• 1193-18-6 3-methylcyclohexen-2-one 

Relevant articles and documents

Engineering anthracycline biosynthesis toward angucyclines

The biosynthesis pathways of two anthracyclines, nogalamycin and aclacinomycin, were directed toward angucyclines by using an angucycline-specific cyclase, pgaF, isolated from a silent antibiotic biosynthesis gene cluster. Addition of pgaF to a gene cassette that harbored the early biosynthesis genes of nogalamycin resulted in the production of two known angucyclinone metabolites, rabelomycin and its precursor, UWM6. Substrate flexibility of pgaF was demonstrated by replacement of the nogalamycin minimal polyketide synthase genes in the gene cassette with the equivalent aclacinomycin genes together with aknE2 and aknF, which specify the unusual propionate starter unit in aclacinomycin biosynthesis. This modification led to the production of a novel angucyclinone, MM2002, in which the expected ethyl side chain was incorporated into the fourth ring.

Synthesis of angucyclines. 8. Biomimetic-type synthesis of rabelomycin, tetrangomycin, and related ring B aromatic angucyclinones

The angucyclinones with aromatic ring B (1a-c and 2a-c) are prepared in a biomimetic-type synthesis by two successive aldol cyclizations starting from the substituted naphthoquinones 12a-c. In both cyclization steps the C-H acidity of the potential nucleophilic centers determines the mode of cyclization under kinetically controlled conditions. The tetrahydroanthraquinones 13a-c/14a-c are hydroxylated at C-4 to the phenolic anthraquinones 16a-c upon treatment with excess NMO.

Synthetic Angucyclines, 3. First Total Synthesis of rac-Rabelomycin by Diels-Alder Reaction

Conjugate addition of the 2-siloxydienes 5a and 5b to juglone (4a) or 3-chlorojuglone (4b) affords the products 6-8a and 8b, respectively.The reaction of 4a with furan 10 yields the substitution product 11, which is converted to the 5-hydroxybutenolide 12