Part of Percy Julian's synthesis of physostigmine is shown below. Which set of reagents could accomplish this sequence? NH2 Me Me Me но. Eto, Eto. CN Me EtO. N. 'N. N. Me Me Me Me

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Part of Percy Julian's synthesis of physostigmine is shown below. Which set of reagents could accomplish this sequence?
NH2
Me
Me
Me
Eto.
CN
iii
Me
но.
Eto,
ii
EtO.
'N.
N.
Me
Me
Me
Me
O i, Etl/NAOH; ii, NaOEt/CICH2CN; iii, Pd/H2
i, Etl/NAOH; ii, NaOEt/CH3CN; iii Pd/H2
also shiw mechanism
O i, Etl/NAOH; ii, NaOEt/CICH2CN; iii, HCI
O i, ELOH/NaOH; ii, NaOEt/CICH2CN; iii, Pd/H2
O i, Etl/NAOH; ii, NaCl/CICH2CN; ii, Pd/H2
Transcribed Image Text:Part of Percy Julian's synthesis of physostigmine is shown below. Which set of reagents could accomplish this sequence? NH2 Me Me Me Eto. CN iii Me но. Eto, ii EtO. 'N. N. Me Me Me Me O i, Etl/NAOH; ii, NaOEt/CICH2CN; iii, Pd/H2 i, Etl/NAOH; ii, NaOEt/CH3CN; iii Pd/H2 also shiw mechanism O i, Etl/NAOH; ii, NaOEt/CICH2CN; iii, HCI O i, ELOH/NaOH; ii, NaOEt/CICH2CN; iii, Pd/H2 O i, Etl/NAOH; ii, NaCl/CICH2CN; ii, Pd/H2
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