Chemistry of quinones. Part 7. Synthesis of anthracyclinone analogues via Diels–Alder reactions of 1,4-anthraquinones
- 1 January 1981
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 689-696
- https://doi.org/10.1039/p19810000689
Abstract
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).This publication has 3 references indexed in Scilit:
- Studies related to anthracyclines. Part 1. Some Diels–Alder reactions of 4a,9a-epoxy-4a,9a-dihydroanthracene-1,4,9,10-tetroneJournal of the Chemical Society, Perkin Transactions 1, 1980
- Daunomycinone analogues via the Diels-Alder reaction. Synthesis and chemistry of some 6,11-dihydroxy-5,12-naphthacenedionesThe Journal of Organic Chemistry, 1976
- SYNTHESIS AND ANTITUMOR ACTIVITY OF 4-DEMETHOXYDAUNORUBICIN, 4-DEMETHOXY-7,9-DIEPIDAUNORUBICIN, AND THEIR BETA-ANOMERS1976