78173-89-4

Usage

InChI:InChI=1/C21H18O8/c1-21(28)7-12(23)14-9(16(21)20(27)29-2)6-10-15(19(14)26)18(25)13-8(17(10)24)4-3-5-11(13)22/h3-6,12,16,22-23,26,28H,7H2,1-2H3/t12-,16-,21+/m0/s1

Upstream product

• 78173-93-0 (+/-)-7-deoxyauramycinone 
• 81418-41-9 1-(1-hydroxy-4,8-dimethoxynaphthalen-2-yl)ethanone 
• 95455-94-0 5-methoxy-3-(5-oxohexanoyl)-1,4-naphthoquinone 
• 95456-09-0 3-acetyl-1,5-dimethoxy-4-methoxymethoxynaphthalene 
• 95456-10-3 3-(5,5-ethylenedioxy-2-hexenoyl)-1,5-dimethoxy-4-methoxymethoxynaphthalene 
• 95455-99-5 methyl 4-(1'-t-butyldimethylsilyloxy-4'-hydroxy-5'-methoxy-3'-(5''-oxohexanoyl)naphth-2'-yl)-2-butenoate 
• 95455-86-0 (+/-)-4-O-methyl-7-deoxyauramycinone 
• 95455-52-0 (+/-)-7-deoxy-5,7-di-O-ethyl auramycinone 
• 95455-76-8 methyl (6a-SR,9-RS,10-RS,10a-RS)-12-t-butyldimethylsilyloxy-5,9-dihydroxy-4-methoxy-9-methyl-6-oxo-6,6a,7,8,9,10,10a,11-octahydronaphthacene-10-carboxylate 

Relevant academic research and scientific papers

Synthesis of (+/-)-aklavinone and (+/-)-auramycinone via electrondeficient o-quinonoid pyrones

Dehydration of the formyl acid 3 (R = H) with acetic anhydride in benzene at 80 deg C generates the quinonoid pyrone 4 which can be trapped with norbornadiene, N-phenylmaleimide and enol silyl ethers; the adduct 6 (R = Me, P = TES) and its 9-epimer 10 from 2-(triethylsilyloxy)propene are readily transformed into (+/-)-auramycinone 2 (R = Me) whilst those from 2-(triethylsilyloxy)buta-1,3-diene are readily converted into the methyl ethers 24, 25, 33 and 34 of which 24, 33 and 34 are known to be readily converted into (+/-)-aklavinone 2 (R = Et).

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