Isobenzofuran route to anthracycloquinones

Details Isobenzofuran route to anthracycloquinones Isobenzofuran route to anthracycloquinones

1978-04-06

1979-05-15

Garvin, Patrick

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260365, 560139, 260351, 260396R, 26034671, C07C 4962, C07C 4970, C09B 362, C07D30769

Patent

active

041547454

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:
patent: 3109007 (1963-10-01), Blackwood et al.
patent: 3518282 (1970-01-01), Schaller et al.
patent: 3665018 (1972-05-01), Jolles
patent: 4012448 (1977-03-01), Smith et al.
patent: 4020270 (1977-04-01), Arcamone et al.

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