Development of new methods in tetrahydropyran ring synthesis : application to enantioselective synthesis of natural products
Chan, Kok Ping
Date of Issue2007
School of Physical and Mathematical Sciences
Prins cyclization is one of the most convergent strategies for the synthesis of 2,6-disubstituted tetrahydropyran rings from homoallylic alcohols and aldehydes. However, several limitations, such as the possibility of racemization of the homoallylic alcohol and substrate compatibility, have rendered this methodology a less preferred choice in the total synthesis of natural products containing the THP motifs. The emphasis of this thesis is placed on the evolution of a novel catalytic Prins cyclization to overcome these current limitations, and manifestation of its applicability to the enantioselective synthesis of natural products.
DRNTU::Science::Chemistry::Organic chemistry::Organic synthesis