Task: make_5_lvl2
Environment: retrosynthesis (level_2 task)
Description: Propose a retrosynthesis route to synthesize the molecule with SMILES O[C@H]1C[C@@H](O[C@@H]([C@@H]1C)/C=C(CO)/C)C/C=C/C=C/C(O)=O. The route must have 5 reactions.

Here are some guidance to help you (the reactions are enumerated in the order that they must be applied): tert-Butyldimethylsilyl (TBS or TBDMS) is a common protecting group for alcohols in organic synthesis. It is introduced using reagents such as tert-butyldimethylsilyl chloride (TBDMSCl) or tert-butyldimethylsilyl trifluoromethanesulfonate (TBDMSOTf) in the presence of a base like imidazole or pyridine. The TBS group is stable under a variety of reaction conditions, including acidic and basic environments, making it useful for multi-step syntheses. It can be removed (deprotected) using fluoride sources such as tetrabutylammonium fluoride (TBAF) or by acidic hydrolysis, regenerating the free alcohol. As a result of this reaction, a bond between oxygen and silicon is broken, and a 'aliphatic hydroxyls' functional group is formed, and a 't-butyldimethylsilyl' gone.

In the Horner-Wadsworth-Emmons reaction, the reaction of aldehydes or ketones with stabilized phosphorus ylides (phosphonate carbanions) leads to olefins with excellent E-selectivity. The overall of the reaction is a carbon-carbon bond formed, while a carbon-phosphorus bond and a carbon-oxygen are broken. As a result, an 'aliphatic carboxylic acid', and  'C-C double bonds' groups are formed.

DIBAL-H is a reducing agent used in organic synthesis, particularly for the selective reduction of esters and nitriles to aldehydes. It is a complex of diisobutylaluminum hydride and is typically used in low temperatures to minimize side reactions. Overall a carbon-oxygen bond is broken, and a another carbon-oxygen bond order changes from 2 to 1, forming a 'aliphatic hydroxyls' functional group.

TMSOTf can be used to protect alcohols by converting them into their corresponding trimethylsilyl (TMS) ethers. The reaction typically involves the treatment of the alcohol with TMSOTf in the presence of a base, such as triethylamine or pyridine. During the reaction a oxygen-silicon bond is broken and another one (O-Si) is formed. No functional groups are formed in the transformation, but the most notable broken is 'aliphatic hydroxyls'.

The Still-Gennari reaction is a modification of the Horner-Wadsworth-Emmons (HWE) reaction that allows for the selective formation of (Z)-alkenes from aldehydes and phosphonate esters. The reaction typically involves the use of a phosphonate ester with electron-withdrawing groups, such as bis(trifluoroethyl) or bis(2,2,2-trifluoroethyl) groups, which helps to stabilize the carbanion intermediate formed during the reaction. Thus, a carbon-carbon double bond, and a carbon-oxygen are formed, while a carbon-phosphorus bond, a carbon-carbon bond and a carbon-oxygen bond are broken. Additionally, the triple bond of an alkyne is changed to a single bond. As a result 'C-C double bonds' and  'carboxylic esters' functional groups are formed.. 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-]"
        }
      ]
    }
  ]
}`.