An efficient three-step method for appending a 2,3-anthracene moiety to the 9,lO-positions of an existing anthracene moiety is described. The first step uses excess 1,4-anthraquinone (3 equiv) and aluminum chloride (6 equiv) to obtain the anthracene-quinone cycloadduct (omission of the AlCl, resulted in no adduct). The resulting diketone was reduced to the corresponding diol (excess LiAlH,), which was dehydrated to the arene with phosphorus oxychloride and pyridine. Specific examples include the preparation of heptipycene 8 from pentiptycene 6 (66% overall yield) and a similar conversion of 8 to the noniptycene 13 (75% overall yield). The methodology led to a markedly improved synthesis of tritriptycene 9 and the first synthesis of undecaiptycene 14.(1) Hart, H.; Shamouilian, S.; Takehira, Y. J . Org. Chem. 1981, 46, (2) Hart, H.; Bashir-Hashemi, A.; Luo, J.; Meador, M. A. Tetrahedron (3) The fused groups may be 9,lO-anthradiyl itself, or analogues such 4427-4432. 1986,42, 1641-1654. as 5,12-naphthacenyl, etc. (4) Hart, H.; Raju, N.; Meador, M. A.; Ward, D. L. J. Org. Chem. 1983, 48,4357-4360. Bashir-Hashemi, A.; Hart, H.; Ward, D. L. J. Am. Chem. SOC. 1986, 108, 6675-6679. Luo, J.; Hart, H. J. Org. Chem. 1987, 52, 3631-3636. ( 5 ) Huebner, C. F.; Puckett, R. T.; Brzechfta, M.; Schwartz, S. L.