58976-87-7Relevant academic research and scientific papers
Combined Multiple Claisen Rearrangement and Ring-closing Metathesis as a Route to Naphthalene, Anthracene, and Anthracycline Ring Systems
Chattopadhyay, Shital K.,Pal, Benoy K.,Maity, Susama
, p. 1190 - 1191 (2007/10/03)
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
Gupta, Dharmendra N.,Hodge, Philip,Khan, Naeem
, p. 689 - 696 (2007/10/02)
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).
