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Total Syntheses of Borolithochromes A, D and G
Kanade Kirita1, Hirotake Matsumoto1, Gaku Endo1
1Department of Applied Chemistry, Faculty of Science and Engineering, Waseda University, 3-4-1 Ohkubo, Shinjuku-ku, Tokyo, 169-8555, Japan.
Abstract:
Total syntheses of borolithochromes A, D and G, red pigments isolated from fossils of Jurassic putative red alga Solenopora jurassica, have been achieved. The benzo[gh]tetraphene skeletons of the borate ligands in these substances were constructed using Diels-Alder reactions of aryl dienes with naphthoquinone, followed by intramolecular Corey-Chaykovsky reactions. Complexation of these ligands with trimethyl borate generated homocomplexes, which upon sequential O-demethylation produced borolithochromes A and G. In the route to borolithochrome D, a heterocomplex was prepared by stepwise complexation of the ligands with 2-(dimethylamino)ethyl dimethyl borate. The strategy devised to accomplish the first total synthesis of borolithochromes A, D and G should be applicable to the preparation of other borolithochromes as well as spiroborates possessing two fused polycyclic aromatic ligands.
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