WORKED PROBLEMS
615
(d) Enantiomer.
OR
O
OH
NH
O
Ph
Ph
change the configuration at
both centres; change dot-wedge
representation rather than
trying to draw mirror image
(e) Alcohol plus acetic anhydride gives acetyl ester.
O
H 3 C
O
CH 3
O
note the nitrogen is part of an amide;
it is not nucleophilic and does not react
OH
taxol
O
H 3 C
O
CH 3
O
O
H
O
H 3 C
O
CH 3
O
O
H
O
H 3 C
O
H
O
H 3 C
O
acetyl ester
O
CH 3
O
nucleophilic attack of alcohol
onto anhydride carbonyl
carbonyl reformed with loss
of acetate leaving group
(f) Note that ester and amide functions were identified in section (a); acidic hydrolysis (hot aqueous HCl) would
lead to acid plus alcohol from ester, acid plus amine from amide. There will be three products. You are not
asked for any mechanisms.
OR
O
OH
NH
O
Ph
Ph
ester
amide
HCl / H 2 O
heat
OH
O
OH
NH 2
O
Ph
Ph
OH
HOR
Problem 16.02 (level 1; chapters 3 and 7)
Fluvastatin is an inhibitor of the cholesterol biosynthetic pathway and may be used to reduce the risk of coronary
conditions, e.g. strokes and heart attacks, in susceptible patients. It has the structure shown, though drug material
is supplied as the racemic form. A partial numbering system is given, and the rest of the molecule may be
abbreviated to ‘aryl’ in answers.
N
F
CO 2 H
OH OH
fluvastatin
2
4
6
7
1
3
5