Chemistry Letters p. 1057 - 1060 (1982)
Update date:2022-08-04
Topics:
Agarwal, Nand L.
Sheeren, Hans W.
The Diels-Alder type cycloaddition of several substituted buta-1,3-dienes with 9-chloro-10-hydroxy-1,4-anthraquinone (10) affords an efficient, regiospecific access in two steps to tetracyclic ketones (12-14) which have been investigated as intermediates for the synthesis of anthracycline derivatives.Butadienes with a less asymmetric ?-electron distribution than 9 give lower regiospecificity in cycloadditions with 10.Depending on the substituents in the used butadiene, the obtained cycloadducts are transformed under the reaction circumstances into the aromatized products (15-20).
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