(1) Predict the major product from each reaction. If you expect no reaction, indicate.
note: aqueous work-up is implied for all reactions.
(a)
EtO2C
CO2Et
2) HCl, H2O, heat
NHAc
OAc
(b)
O
AcO
AcO
(c)
1) LDA, PhCH2Br
AgNO3
OH
Br
OR
OR
OR
KOH
O
haet
R=CH3(CH2)14C
OH
(d)
O
1) Br2, PBr3
2) NH3 (excess)
O
O
(e)
Ph
OH
NHBOC
N
(f)
O
OMe
CO2Et
NH2
DCC
N
H
O
1) NH3, HCN
OMe
(g)
CHO
2) HCl, H2O
O
O
(h)
O
NH3, NaCNBH3
(2) Give a detailed mechanism for the following reaction, show all steps.
OAc
OAc
AcO
OAc
O
OAc
1) HCN
AcO
OAc
O
Ph
2) LDA, PhCH2Br
3) MeOH, HCl
OMe
(3) Complete the following roadmap problem.
O
1) mCPBA
3) TMSCl, Et3N
2) NaN3
4) H2, Pd/C
4) FMOC-Cl, pyridine
6) Piperidine
5) NH2OCH3
7) CH2O, NaCNBH3
HOAc
10) OAc
AcO
8)Ac2O, pyridine
9) TBAF
OAc
O
Br
AgNO3
11) NaOH
(4) Propose a mechanism for the following enzymatic transformation
neryl pyrophospahte
enzyme
(5) For the following aminosugar, draw the enantiomer
H2N
HO
H
H
CHO
H
H
OH
OH
CH2OH
(6) Draw this compound in the chair form.
(7) Give the product and a mechanism for the following reaction.
O
1) TFA
MeO
NHBOC
O
2) NaCNBH3
HOAc
(8) Using benzene and and any other organic reagents with less than six-carbons, design a synthesis of the
following unnatural amino acid.
O
OH
NHFMOC
OMe