Thesis-Final 03 June 2011 pdf - Jacobs University

Conclusions Chapter 4
The products produced from 1-(β, β, β-trichloroethoxycarbonyl) quinide
The acylation method which was established by Sefkow and his group was also
applied to synthesis of Troc protected quinide derivatives. The only the difference
between acylating acetal protected quinide and Troc protected quinide reactions was
the starting materials. The same principle of the method was applied to both type of
reactions. The Troc protecting group hasn’t removed from all of the synthesised
compounds. But, the way to remove the Troc protection by using zinc powder was
already established in the literature. In this thesis it was proven (by the reaction 80
and 88) that the same method works without any problem during the synthesis of the
chlorogenic acids. Therefore, for some of the compounds removal of the Troc
protection was left out but at least the way to make the pure compounds available was
established. The list of the products synthesised from 1-(β, β, β-
trichloroethoxycarbonyl) quinide, (48) as shown below;
O
O
O
O
O
O
O
O
O
OH
O
O
O
O
O
OH
O
O
O
O
O
OH
O
O
CCl 3
CCl 3
CCl 3
OMe
OMe
(74)
(75)
OMe
(76)
OAc
O
O
O
O
O
O
O
O
O
O
O
OH
O
O
O
O
O
OH
O
O
O
O
O
O
O
OH
HO
O
O
OH
CCl 3
CCl 3
CCl 3
OAc
OAc
OAc
OAc
OAc
OAc
OAc
(77)
(78)
(79)
(80)
Figure 138: Troc protected chlorogenic acid lactones
175