58976-90-2

Upstream product

• 77972-71-5 5,12-diacetoxy-2,3-dibromo-1,2,3,4-tetrahydronaphthacene-6,11-dione 
• 58976-81-1 1,4,4a,12a-Tetrahydro-naphthacene-5,6,11,12-tetraone 
• 64-19-7 acetic acid 
• 92979-06-1 2,3-diallyl-9,10-dioxo-9,10-dihydroanthracene-1,4-diyl diacetate 
• 1709-63-3 anthracene-1,4,9,10-tetraone 
• 77972-52-2 1,4,4a,12a-tetrahydronaphthacene-5,12-dione 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 77972-63-5 5,12-diacetoxy-1,4-dihydronaphthacene 
• 79207-97-9 1,4-bis(prop-2'-enyloxy)-9,10-anthraquinone 
• 79208-01-8 2,3-diallyl-1,4-dihydroxyanthraquinone 

Downstream Products

• 58976-87-7 1,4-dihydro-5,12-dihydroxynaphthacene-6,11-dione 
• 58976-89-9 1,4-dihydro-5,12-dimethoxynaphthacene-6,11-dione 
• 58977-08-5 1,2,3,4-tetrahydro-2,5,12-trihydroxynaphthacene-6,11-dione 
• 58977-07-4 7,8,9,10-Tetrahydro-9-hydroxy-6,11-dimethoxy-5,12-naphthacenedione 

Relevant academic research and scientific papers

Formation of arenes via diallylarenes: Strategic utilization of Suzuki-Miyaura cross-coupling, Claisen rearrangement and ring-closing metathesis

Two new synthetic strategies for benzoannulation are reported. The first strategy is based on the Suzuki-Miyaura cross-coupling reaction. To this end, various ortho-diallylbenzene derivatives were prepared from the corrresponding diiodo derivatives by an allylation strategy using an allylboronate as coupling partner. These diallyl derivatives were subjected to a ring-closing metathesis (RCM) and one-pot dichlorodicyanoquinone (DDQ) oxidation sequence to deliver 2-substituted naphthalenes. In the second strategy, a double Claisen rearrangement and RCM protocol have been used as key steps to give highly functionalized benzoannulated quinone derivatives.

A new protocol for benzoannulation by double Claisen rearrangement and ring-closing metathesis reactions as key steps

A new methodology for benzoannulation has been developed by using double Claisen rearrangement followed by a one-pot ring-closing metathesis and DDQ oxidation sequence.

Chemistry of Quinones. Part 7. Synthesis of Anthracyclinone Analogues via Diels-Alder Reactions of 1,4-Anthraquinones

Diels-Alder adducts were formed by reaction of 1,4-anthraquinone with buta-1,3-diene, with 1-acetoxy-, 1-methyl-, 2-methyl-, and 2,3-dimethyl-buta-1,3-diene, and with cyclohexa-1,3-diene.Adducts were also prepared by reaction of 9-chloro-10-hydroxy-1,4-anthraquinone with buta-1,3-diene and with 2-methylbuta-1,3-diene.Some of the linear tetracyclic adducts were transformed to 1,2,3,4-tetrahydro-1,5,12-trihydroxynaphthacene-6,11-quinone (21) and 2-acetyl-1,2,3,4-tetrahydro-2,5,12-trihydroxynaphthacene-6,11-quinone (7).The latter has been converted by other workers into 4-demethoxydaunomycinone (48) and 4-demethoxydaunomycin (8).