+44 (0)1509 263171
Please use this identifier to cite or link to this item:
|Title: ||Studies toward the synthesis of the guaianolide skeleton: an intramolecular hetero Diels Alder approach and a carbonyl ene approach|
|Authors: ||Gambera, Giovanni|
The intramolecular hetero Diels Alder
The intramolecular carbonyl ene reaction
|Issue Date: ||2006|
|Publisher: ||© Giovanni Gambera|
|Abstract: ||This thesis describes the efforts towards the synthesis of the guaiane-6,12-olide
skeleton, which characterises the guaianolide family of bioactive natural
compounds. Two approaches have been investigated: the intramolecular hetero
Diels Alder (IMHDA) reaction and the intramolecular carbonyl ene reaction.
This thesis has been divided in three sections: the first part gives a general
background about the guaianolides, the second section describes the synthetic
approaches we investigated and, finally, the third section reports the experimental
The first section gives a brief overview about the biosynthesis, the biological
activities of the guaianolides, and the most interesting synthetic approaches to
The second section describes the two different approaches we investigated and
gives a theoretical background about the main chemical transformations used.
At first, the IMHDA reaction approach is described: a brief overview of
palladium catalysis and Diels Alder reaction is given, and it is followed by the
results and discussion of our study.
Similarly, a theoretical background of the Alder ene reaction is given, before the
results and discussion of the intramolecular carbonyl ene reaction approach are
described: particular importance is given to the reasoning that led to the
assignment of the relative configuration of the cycloadducts obtained, and to the
rationalisation of this stereochemical outcome.
Finally, the third section gives a complete description of the experimental
procedures followed, and of the experimental data for the synthetic studies
performed in the previous chapter.|
|Description: ||A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy of Loughborough University.|
|Appears in Collections:||PhD Theses (Chemistry)|
Files associated with this item:
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.