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Synfacts 2006(10): 1010-1010  
DOI: 10.1055/s-2006-949359
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Dodecamethoxy- and Hexaoxotricyclo-butabenzene

Contributor(s): Timothy M. Swager, Mark S. Taylor
T. Hamura, Y. Ibusuki, H. Uekusa, T. Matsumoto, J. S. Siegel*, K. K. Baldridge, K. Suzuki*
Tokyo Institute of Technology and Science and Technology Corporation, Tokyo, Japan; University of Zurich, Switzerland
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Publication History

Publication Date:
21 September 2006 (online)

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Significance

The synthesis of novel tricyclobutabenzene derivatives 7 and 8 is reported. Iodophloroglucinol derivative 1 served as a benzotriyne equivalent in this sequence, in which cycloadditions of benzynes and silyl ketene acetals were employed as the key carbon-carbon bond-forming events. The selective generation of benzyne from dibromide 4, and the regioselectivity at work in the formation of 3, 5, and 6 highlight the utility of such [2+2] cycloadditions for complex target synthesis.