Which synthesis scheme would provide the best yield of the target compound
Which synthesis scheme would provide the best yield of the target compound? Assume an aqueous workup after each step.
1. CH3-Li (2 equivalents) 2. Mild acid, gentle heat, remove water 1. TBDMS-Cl, pyridine 2. CH3-Li (2 equivalents) 3. POCl3, pyridine 4. Mild acid, gentle heat, remove water 1. LiAlH4 2. PBr3 3. Mg, ether followed by CO2 4. Mild acid, gentle heat, remove water 1. Ethylene glycol, mild acid, remove water 2. CH3-Li (2 equivalents) 3. PBr3 4. Mg, ether followed by CO2 5. Mild aqueous acid 6. Mild acid, gentle heat, remove water 1. (CH3)2NH, mild acid, remove water 2. LiAlH4 3. Ph3P ylide with acetone 4. Na2Cr2O7, aqueous acid 5. Mild acid, gentle heat, remove water
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