5,12-Epoxy-naphthacene-6,11-dione derivatives

Details 5,12-Epoxy-naphthacene-6,11-dione derivatives 5,12-Epoxy-naphthacene-6,11-dione derivatives

1977-05-02

1978-09-26

Jiles, Henry R.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260376, 260396R, 560107, 560255, 26034342, C07D30787

Patent

active

041169816

ABSTRACT:
There is provided a novel method of synthesizing certain tetracyclic quinones. In particular, there is provided a novel route to the synthesis of (+)-7-deoxydaunomycinone and analogs thereof which includes the provision of novel tetrahydronaphthoquinones and tetracyclic quinone intermediates. The compounds of the present invention are provided through a route comprising a Diels-Alder addition of certain isobenzofurans to certain novel tetrahydronaphthoquinones. The products of the synthetic route provided herein may be converted into compounds of known antibiotic and antineoplastic activity.

REFERENCES:
fieser et al., Canadian Journal of Chem. 43, 1599-1606, (1965).
Bergmann, J. of Chem. Society 1147-1150 (1938).

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