difficulties. To the contrary, it has been our experience over the last 6 years that these molecules can be readily synthesized and are easy to handle. And with the generality of the quinone synthesis described herein, it is anticipated that newer, even simpler methods of cyclobutenedione synthesis will be explored in the near future. By combining the chemistry described in this manuscript with the numerous procedures known for directed metalation of aryl and heterocyclic systems,15 a powerful procedure is at hand for the synthesis of quinone based biologically active molecules.Acknowledgment. This investigation was supported by PHS Grant CA 40157 awarded by the National Cancer Institute, DHHS. We are grateful to Professor Harold Moore of U.C. Irvine for communicating his results to us prior to publication and to Dr. Romanworq Ferede and Mr. Charles McSwain for their efforts on the project. Supplementary Material Available: Complete experimental details for the synthesis of the compounds described in this manuscript (13 pages). Ordering information is given on any current masthead page.
A general regiospecific synthesis of annulated hydroquinones /quiñones is presented. This specifically involves the thermal rearrangement of the 4-aryl-4-hydroxycyclobutenones la-k to the corresponding annulated hydroquinones. The synthetic scope and mechanism of this rearrangement are discussed.Reported here are the details of a general, convergent, regiospecific and high-yield synthesis of annulated hydroquinones and quiñones.1,2 It involves the thermal rearrangement of 4-aryl-4-hydroxycyclobutenones 1 to the corresopnding hydroquinones, which were generally not
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