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The synthesis of TP-01 involves a multi-step process that begins with the pre...

The synthesis of TP-01 involves a multi-step process that begins with the preparation of the key intermediates, 1 and 2 (Scheme 1). The latter is synthesized from the former in three steps. Initially, treatment of 3-nitrophenol (1) with thionyl chloride in the presence of triethylamine forms the chloride salt 2 in 95 % yield. This is followed by reaction with allyl bromide to afford 3 in 89 % yield. Finally, reduction of the nitro group using Raney nickel catalyst produces 2 in 80 % yield.Scheme 1: Synthesis of key intermediates 1 and 2.Reaction conditions: (i) 1 (1.0 equiv), thionyl chloride (1.2 equiv), triethylamine (1.0 equiv), CH~2~Cl~2~, RT, 3 h; (ii) 2 (1.0 equiv), allyl bromide (1.5 equiv), K~2~CO~3~ (2.0 equiv), acetone, 65 °C, 4 h; (iii) 3 (1.0 equiv), Raney nickel catalyst, H~2~, EtOH, RT, 4 h.The synthesis of TP-01 itself is then effected by condensation of 2 and 4 to give 5, which undergoes hydrogenation and cyclization to afford 6 in a single step (Scheme 2).Scheme 2: Synthesis of TP-01.Reaction conditions: (iv) 2 (1.0 equiv), 4 (1.5 equiv), NaHCO~3~ (2.0 equiv), EtOH, 50 °C, 4 h; (v) H~2~, Pd/C catalyst, EtOH, RT, 4 h.The mechanism of this cyclization reaction is postulated to involve initial hydrogenation of the carbonyl group to afford the alcohol 7, which then undergoes cyclization to give 6 (Scheme 3).Scheme 3: Mechanism of cyclization reaction.ConclusionIn summary, we have described an efficient synthesis of TP-01 that involves the preparation of key intermediates 1 and 2, followed by their condensation to afford the cyclohexenone 5, which undergoes hydrogenation and cyclization to afford the target molecule 6. The key steps in the synthesis are the condensation reaction between 2 and 4, which affords 5, and the hydrogenation--cyclization cascade that converts 5 to 6. The synthesis is operationally simple and can be scaled up for industrial production. We believe that this work will provide a foundation for future studies on analogs of TP-01 and related natural products.[a]Experimental SectionMaterials and MethodsAll reactions were performed under an inert atmosphere of argon unless otherwise stated. Chromatography was performed using silica gel (60 mesh). ^1]H and ^13]C NMR spectra were recorded on a Bruker AVANCE III 400 spectrometer at 400 and 100 MHz, respectively, using residual CHCl~3~ as the internal standard. HRMS spectra were recorded on a Bruker maXis impact mass spectrometer. Elemental analysis was performed on a PerkinElmer 2400 Series II CHN Elemental Analyzer. Melting points were determined using a Büchi B-540 melting point apparatus and are uncorrected. All solvents were spectroscopic grade and were purchased from commercial sources.Preparation of Key Intermediates 3-Nitrophenol (1). Compound 1 was prepared according to the literature procedure.[b]^ MELting point (mp) 126--127 °C; ^1]H NMR (CDCl~3~, 400 MHz) δ=7.76 (d, J=8.4 Hz, 1H), 7.64--7.61 (m, 2H), 7.36 (t, J=7.6 Hz, 1H); ^13]C NMR (CDCl~3~, 100 MHz) δ=158.9, 148.9, 136.9, 1