- The use of 1,4-dipolar aryne cycloaddition strategy in anthracyclinone synthesis: The formal synthesis of (±)-4-demethoxydaunomycinone
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We report herein the convergent synthesis of the 7,8,9,10-tetrahydro-9-hydroxy-6,11-dimethoxy-5,12-naphthacenedione (9), an advanced intermediate in the synthesis of (±)-4-demethoxy-daunomycinone, using the aryne dipolar cycloaddition reaction of lithiated 3-cyanophthalide and 2-bromo-5,6-dihydro-1,4-dimethoxynapththalene (6) in the key step. Similarly, the non-convergent synthesis of the 7,8-dihydro-4,6,11-trimethoxy-5,12-naphthacenedione (10), an important intermediate in the synthesis of (±)-daunomycinone, is presented.
- Khanapure,Biehl
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- Chemistry of Quinones. Part 7. Synthesis of Anthracyclinone Analogues via Diels-Alder Reactions of 1,4-Anthraquinones
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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).
- Gupta, Dharmendra N.,Hodge, Philip,Khan, Naeem
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p. 689 - 696
(2007/10/02)
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