Reaction of 1, 1-dimethylindene-3-carbonyl chloride (9), prepared from 3, 3-dimethylindanone (5) via a four step sequence, with ethyl 3-(N-tert-butoxycarbonyl-N-methyl)aminopropionate (14)or its 2-methyl derivative (15) in the presence of lithium diisopropylamide (LDA) gave the β-keto esters (16 and 17). De-tert-butoxycarbonylation of 16 followed by treatment with sodium bicarbonate did not give 12, while 17 afforded the cyclized β-keto ester (19) in good yield. Sodium borohydride reduction of 19 followed by treatment with methanesulfonyl chloride gave the mesylate (21), which was reacted with 1, 8-diazabicyclo[5.4.0]-7-undecene (DBU) to give the unsaturated ester (22). By analogous reaction sequences, the diethylamide derivative (2) was synthesized in moderate yield. Reaction of the β-keto ester (16) with diethyl phosphorochloridate in the presence of LDA gave the enolphosphate (30), which was converted to the unsaturated esters (31a and 31b) in good yields. However, dephosphorylation of 31 failed. Sodium borohydride reduction of 16 gave the alcohol (33), which was converted to the diene ester (34) or the mesylate (36). These were successfully converted to the ethyl 1, 2, 3, 9a-tetrahydro-9H-indeno[2, 1-b]pyridine-3-carboxylates (32s and 32b), which were found to exist in an equilibrium mixture, in excellent yields, respectively. The stereochemistry of some of the key intermediates and of the target compounds is discussed.