Task: make_8_lvl2
Environment: retrosynthesis (level_2 task)
Description: Propose a retrosynthesis route to synthesize the molecule with SMILES O=S(NC1=CC(N2CCN(C(OC(C)(C)C)=O)CC2)=C3C(CCC4(CCC4)O3)=C1)(C5=C(F)C=CC=C5)=O. The route must have 6 reactions.

Here are some guidance to help you (the reactions are enumerated in the order that they must be applied): An aromatic amine attacks the electrophilic sulfur of phenylsulfonyl chloride, then the intermediate collapses to expel Cl⁻ and base deprotonates the N-H to give the sulfonamide. 'sulfonamides' functional group is formed, (N-S bond) while a (S-Cl bond) is broken.

The reduction of nitro groups to amines can be achieved using various reducing agents. Common methods include catalytic hydrogenation (using hydrogen gas and a metal catalyst such as palladium on carbon, Pt, or Raney nickel) or chemical reduction using reagents like iron and hydrochloric acid (Fe/HCl), tin and hydrochloric acid (Sn/HCl), or zinc and ammonium chloride (Zn/NH4Cl). These methods effectively convert the 'nitro' group (-NO2) to an 'primary amines' group (-NH2) while preserving other functional groups in the molecule, and a bond between O and N being broken during the process.

During an Nucleophilic Aromatic Substitution (S_NAr) reaction, a nucleophile replaces a leaving group (such as a halogen) on an aromatic ring. This reaction typically occurs when the aromatic ring is activated by electron-withdrawing groups (like nitro groups) that stabilize the negative charge in the intermediate Meisenheimer complex. The nucleophile attacks the carbon atom bearing the leaving group, leading to the formation of a new carbon-nucleophile bond and the departure of the leaving group. For example, when the nucleophile is an amine, a carbon-nitrogen bond is formed while a carbon-halogen bond is broken, breaking an 'halide' functional group.

The Electrophilic Bromination of an aromatic ring involves the substitution of a hydrogen atom on the aromatic ring with a bromine atom. This reaction is typically carried out using bromine (Br2) in the presence of a Lewis acid catalyst, such as iron(III) bromide (FeBr3) or aluminum bromide (AlBr3). The Lewis acid activates the bromine molecule, generating a more electrophilic species that can attack the aromatic ring, leading to the formation of a new carbon-bromine bond, and an 'halide' functional group is formed.

For fully reducing a ketone into an alkane, the Wolff-Kishner reduction can be employed. This reaction involves the conversion of the ketone into a hydrazone intermediate using hydrazine (NH2NH2) under basic conditions, followed by heating with a strong base (like KOH) to eliminate nitrogen gas and form the corresponding alkane. During the entire process, the O-H bond of the ketone is broken, and obviously a 'ketones' functional group as well.

In the cyclization of chalcones to flavanones, an intramolecular Michael addition occurs where the nucleophilic enolate of the ketone attacks the electrophilic beta-carbon of the alpha,beta-unsaturated carbonyl system. This reaction is typically catalyzed by a base or acid and results in the formation of a new carbon-carbon bond, leading to the cyclic flavanone structure. During the reaction, a C-C and a C-O bond are formed, while a C-O bonds is broken. About the functional groups, a 'ether oxygens' are formed, and 'aromatic hydroxyls' and 'ketones' are broken.. Note that each of the hint describes the forward reactions for each step (enumerated in the order that they should be applied), but you have to perform the retrosynthetic reactions.
Allowed tools: check_smiles_reaction_template_matching, search_template_catalog_by_criteria, get_template, get_available_functional_groups, apply_template, verify_step, verify_route, search_catalog_by_smiles, is_buyable, deprotect_molecule, detect_functional_groups, detect_protection_groups
Submission format: Submit a JSON object representing the retrosynthesis route. It must follow the same JSON format as the next example: `{
  "type": "mol",
  "smiles": "CO",
  "children": [
    {
      "type": "reaction",
      "template_id": 1234,
      "children": [
        {
          "type": "mol",
          "smiles": "BrC"
        },
        {
          "type": "mol",
          "smiles": "[OH-]"
        }
      ]
    }
  ]
}`.