ORGANIC CHEMISTRY 203
SUMMER QUARTER 2004-2005
PROBLEM SET
NAME:
Lycopodine, isolated in 1881, is the most widely distributed alkaloid from the genus
lycopodium. There have been a number of elegant total syntheses of this compound. One of the
earliest was by Gilbert Stork, using his enamine synthesis as a key reaction.
This is a mostly mechanism Problem Set. Each reaction is divided up into small steps.
Provide either reagents or mechanism as indicated. If it is a mechanism step, all reagents are
provided, do not add any.
mechanism
1. MeO OEt NaOEt, EtOH MeO OEt
O O
2. mechanism
MeO OEt
OEt MeO OEt
+ NaOEt, EtOH
O
O O O
EtO
O O
3. mechamism
MeO OEt
MeO O
O NaOEt, EtOH
EtO
O O EtO
O O
4. mechanism
MeO O MeO O
K2CO3, H2O
+ CO2 + EtOH
heat
EtO
O O OH
5. mechanism
MeO O 1. LiAlH4 MeO O
2. H3O+
OH (Think conjugate addition, then elimination)
6. Mechanism
MeO O 1. CH MgBr, CuCl MeO O
3 2
(Gilman reagent)
2. dilt. H+
7. reagents
MeO O ? MeO N
O NH2
8. mechanism O
NH2
MeO N +
MeO N
MeOH
9. mechanism
9. mechanism
O NH2
O
H
N
+
MeO N MeO NH
+
O
H +
MeO NH
redrawn
+
O N
H
OMe
10. mechanism
a cationic cyclization
+
O N O N
H H
OMe OMe
11. mechanism
LiAlH4
reduces amides to amines
O N N
H H
OMe OMe
12. mechanism
Li/ NH3., EtOH
Birch reduction N
N
H H
OMe OMe
13. mechanism
1. KOtBu
2.
N O N
H
Cl O CCl3
OMe O O OMe
(protects amine)
CCl3
14. reagents
?
N Chapter 6
N CHO
O O OMe CO2Me
O O
CCl3
CCl3
15. mechanism
OH
H2O2 (30%) O
N CHO OH
+
N N C OH
CO2Me O
O O CO2Me CO2Me
O O O O
CCl3
CCl3 CCl3
H
N O
O
CO2Me
O O
CCl3
16. mechanism
NaOMe
H
N O N O
O
CO2Me CO2Me
O O O O
CCl3 CCl3
17. mechanism extra credit
Zn, MeOH
N O deprotects amine N O
H
CO2Me CO2Me
O O
CCl3
18. mechanism
+ MeOH
N O O
H N
CO2Me
O
19. reagents
? ?
N O N OH N O
O
Chemistry Homework Solutions
#47082
Arrow pushing
I need help knowing exactly where to push arrows from in one molecule (which bond, carbon etc.) and where it goes to in the next molecule (which carbon, oxygen etc)
I'm just looking to get a good understanding on this example problem set so I have a good understanding of it for future problems. I am just not
sure where exactly the arrow comes from and where it needs to go to. I have quite a bit of trouble with this and am hoping that this example can
be used to help me understand so I can reason it out on another example.
(See attached file for full problem description)
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By OTA - Overall OTA Rating
Siva Kumar, MSc, MPhil - 4.5/5
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