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

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter24: Catalytic Carbon-carbon Bond Formation
Section: Chapter Questions
Problem 24.38P
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Also show the mechanism please 

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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