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Tutorial 2

This document contains 6 questions regarding organic chemistry reactions and syntheses. Question 1 asks about the asymmetric synthesis of amino acids from proline. Question 2 asks about separating enantiomers of the drug tazadolene. Question 3 asks how to make enantiomerically enriched samples of compounds. Question 4 asks about synthesizing the optically active compound "Disparlure". Question 5 asks for structures of intermediates in an asymmetric reaction. Question 6 asks for missing structures in a natural product synthesis and mechanisms.

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Marlinda Marcus Lundang
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241 views3 pages

Tutorial 2

This document contains 6 questions regarding organic chemistry reactions and syntheses. Question 1 asks about the asymmetric synthesis of amino acids from proline. Question 2 asks about separating enantiomers of the drug tazadolene. Question 3 asks how to make enantiomerically enriched samples of compounds. Question 4 asks about synthesizing the optically active compound "Disparlure". Question 5 asks for structures of intermediates in an asymmetric reaction. Question 6 asks for missing structures in a natural product synthesis and mechanisms.

Uploaded by

Marlinda Marcus Lundang
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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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

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