In our continuing study on thallium compounds, such as (3-formylindo1-4-yl)thallium (8a) and (1-acety1-2,3-dihydroindo1-7-yl)thallium bis(trifluoroacetate) (8b), we have elaborated various new regioselective reactions which enable us to convert C-T1 bond in 8a and 8b either to C-C, C-Si, C-X, C-OH, C-N_3, C-NO_2, or C-SCN bond according to our own will. Utilizing above mentioned reactions, the first total synthesis of indole alkaloid, bipolaramide ((-)-5), was achieved in 47% overall yield starting from commercially available (2S)-(-)-2,3-dihydroindole-2-carboxylic acid ((-)-18) in three (or two) steps. Some derivatives, ((-)-22a-c), having dihalogeno or dialkenyl substituents at the 4 and 11 positions of (6aS)-cis-6a,7,13a,14-tetrahydropyrazino[1,2-a:4,5-a']diindole-6,13-dione were also readily prepared.
