searched by RB Woodward and colleagues with goal of synthesizing products Prize
ID: 515868 • Letter: S
Question
searched by RB Woodward and colleagues with goal of synthesizing products Prize and this successful research was one man reasons he was the Nobel in Chemistry in 1965. Extra Due April 26, 4 pm Classify as many reactions as possible with a general specific to add applies that reaction. occasionally one namenype issufficient 24 points available up to 5% to Test 4 The second reaction is classifed in blue italics as an example. 1) NaOH, Dioxane. H,o 2) product seed crystals H3CO H3CO H3CO Base-catalyzed epimerization 1) LIANH H2SO4 2) H, O. 1) Hco.Et, NaoMe Zn KOC(CH,), 2) H,0- okylene, 2) KOH CO H20 (CH),C o 1) Oso CuSO 2) mannitol KOH 1) HCO, Et, NaOMe 2) HO- PdSnCO Key: Ac (acety): CH,c o. Ph phenyo c H, 1: refluxExplanation / Answer
In the answer I have given names of steps per arrow.
Step 1 : The Diels-Alder Reaction
Step 2 : Base catalysed epimerization
Step 3 : Reduction of ketone using LiAlH4
Step 4 : Demethylation from enolate to ketone
Step 5 : Acylation of alcohol as acetic anhydride is used
Step 6 : Zn reduction using phase transfer
Step 7 : Claisen condensation as strong base used and a b-keto aldehyde is formed
Step 8 : Aldol condensation and Michael addition
Step 9 : Osmenium tetraoxide oxidation of alkene to give cis diol
Step 10: Acetal formation for protection of diol
Step 11: Heterogeneous catalytic reduction
Step 12: Claisen condensation
Step 13: Enamine formation using 2o amine and aldehyde
Step 14: Michael addition as C- is addad to b postion of nitrile
Step 15: Hydrolysis of nitrile to give COOH
Step 16: Lacton formation
Step 17: Grignard reaction to open lactone
Step 18: Claisen condensation
Step 19: Oxidetive cleavage of vicinal diol using per-iodic acid
Step 20: Aldol condensation
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