Recently, 3-alkylidenedihydropyrrol-2-ones and 3-alkylidenedihydropyrrole derivatives were synthesized starting from the Baylis-Hillman adducts of methyl acrylate and methyl vinyl ketone, respectively. These compounds were prepared by the reductive cyclization of nitroalkane derivatives, which were synthesized from the Baylis-Hillman acetate by the SN2' reaction with primary nitroalkane, 1,2 as shown in Scheme 1. We reasoned that we could prepare tetrahydropyrrolizine3,5-dione skeleton by using the same nitroalkane derivative 1 as the starting material as shown in Scheme 2. A variety of compounds with tetrahydropyrrolizine-3,5-dione backbone were known and have been synthesized. The overall reaction pathway for the target compound involved sequential introduction of primary nitroalkane at the primary position of Baylis-Hillman adduct to make the starting material 1, Michael addition of 1 to appropriate Michael acceptor 2 to form 3, reduction of the nitro group of 3 and concomitant cyclization to lactam compound 4. From this lactam derivative 4 the desired tetrahydropyrrolizine-3,5dione skeleton 5 could be synthesized. Thus, we prepared 1a from the reaction of the corresponding Baylis-Hillman acetate and nitroethane as reported. The next Michael addition reaction was carried out with methyl acrylate (2a) in the presence of DBU in CH3CN to produce 3a. With this compound 3a in our hands, we examined the reduction of nitro group under Fe/AcOH conditions and obtained 4a (54%). We could not find the other possible lactam compound 4' (Scheme 2). The next cyclization reaction of 4a to the final compound 5a was performed according to method already reported in a similar system, hydrolysis of the ester group and the following lactamization under the influence of acetic anhydride at refluxing temperature. Encouraged by the successful results, we examined the