SCES3120/SIC3002: ORGANIC CHEMISTRY III

SID3002: ADVANCE ORGANIC CHEMISTRY

SEMESTER 2, 2017/2018
TUTORIAL 2

1. Explain how this asymmetric synthesis of amino acids, starting with natural proline, works.
Explain the stereoselectivity of each reaction.

H H H2, Pd
NH3 O CF3CO2H
CO2H O
N N CO2Me N N
H NH NH
O O
(S)-proline O O
HO R
(A) R (B) (C) R

H
O H3O+ HO2C NH
N CO2H +
NH N H R
O H
H R
(E)
(D)

2. This is a synthesis of the racemic drug tazadolene. If the enantiomers of the drug are to be
evaluated for biological activity, they must be separated. At which stage would you advocate
separating the enantiomers and how would you do it?

3. How would you make enantiomerically enriched samples of these compounds (either
enantiomer)?
4. Show how would you synthesis optically active compound called “Disparlure” from the given
starting material?

5. Give the structure of products J-N in the asymmetric reaction shown below. Give the correct
stereochemistry where ever possible.

Ph O Ph O
H2 H2
Et OH Et OH
(J) (R)-BINAP H
(S)-BINAP CH3
Ru(OAc)2 H CH3
Ru(OAc)2

Ph
H2 H2
(K) Et OH (L)
(S)-BINAP CH3 (R)-BINAP
Ru(OAc)2 Ru(OAc)2

6. Reaction scheme shown below are the synthesis pathway of “Apoptotic Natural Myrcene-
Derived Cyclohexenyl Chalcone.
i. Give the structure of the missing intermediate 1, 3, 5, 7, and 9.
ii. Show the mechanism for the conversion of 2 to 3 and 7 to 8.
 LiOH, H2O2
THF, H2O MeONHOMe MeMgBr
(3) O
(5) Bu2O, 0 oC O
OH CH3
(4) (+)-fislatifolione
(6)

Prepared by Prof Azhar

26-02-2018