58976-89-9

Upstream product

• 58976-90-2 5,12-diacetoxy-1,4-dihydronaphthacene-6,11-dione 
• 1709-63-3 anthracene-1,4,9,10-tetraone 
• 58976-81-1 1,4,4a,12a-Tetrahydro-naphthacene-5,6,11,12-tetraone 
• 77972-52-2 1,4,4a,12a-tetrahydronaphthacene-5,12-dione 
• 170024-88-1 2,3-diallyl-1,4-dimethoxyanthraquinone 
• 58976-87-7 1,4-dihydro-5,12-dihydroxynaphthacene-6,11-dione 
• 77-78-1 dimethyl sulfate 
• 77972-71-5 5,12-diacetoxy-2,3-dibromo-1,2,3,4-tetrahydronaphthacene-6,11-dione 
• 77972-63-5 5,12-diacetoxy-1,4-dihydronaphthacene 

Downstream Products

• 58977-07-4 7,8,9,10-Tetrahydro-9-hydroxy-6,11-dimethoxy-5,12-naphthacenedione 
• 58977-08-5 1,2,3,4-tetrahydro-2,5,12-trihydroxynaphthacene-6,11-dione 
• 36831-93-3 5,12-dimethoxy-6,13-tetracenequinone 

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.

Combined Multiple Claisen Rearrangement and Ring-closing Metathesis as a Route to Naphthalene, Anthracene, and Anthracycline Ring Systems

A new route involving double Claisen rearrangement of a suitable 1,4-diallyloxyarene system followed by ring-closing metathesis of the resulting diene has been developed for the synthesis of various benzannulated cyclohexenes. An important demonstration of this methodology is the construction of the tetracyclic quinophenolic ring system of the clinically important anthracyclines.

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).