Solanoeclepin A is the hatching agent of the potato cyst nematode (PCN), an insect which is responsible for destroying 10% of the annual Dutch potato harvest. When the potato fields are not used, the PCN can survive in its dormant state for years. Once it is hatched, though, the insect will die within 8 weeks. The idea has been opted to spread out solanoeclepin A or actually a cheaper analogue over the potato fields before the potato harvest to eliminate all the PCN.
Solanoeclepin A shows hatching activity in concentration as low as 10-9 g/L. The limited information available indicates that the molecule is unstable at pH below 2 and above 7 and at temperatures above ca. 350C.
Because solanoeclepin A is available from potatoes only in very small quantities, it will have to be synthesized. In this thesis, a synthetic pathway is described using the [2+2] photocycloaddition as a key step. The synthetic techniques are very innovative and will enlarge the scope of techniques available for the organic chemist to a very large extent.
In the photochemical reaction of an alkene and an enone, which is used frequently in this research, the ‘rule of five’ –which depicts five-membered rings to form faster than rings of all other sizes when it comes to radical cycloadditions- plays an important rule.
The photochemical outcome in some cases is determined by this rule of five but in one case it does not apply because there is a competiting effect of leaving the most stable radical after the first ring-closure.
At first, model systems are used which are not totally convertible into solanoeclepin A. Then the models are constructed more sophisticated by time. Finally, a set-up is made for how it should be possible to synthesize solanoeclepin A totally.
The other techniques used are also very sophisticated. For instance, the Grubbs catalyst is applied in different systems successfully. An alkylation is done using the mesylate as a leaving group, which is new for the nucleophile concerned.
The main goal of the research is to do innovative synthetic research.Synthetic research insinuates a relationship of a meticulous process of discovering truth contradicted against a fabricated, as in concocted, reality. It is important to realize the logical aspect of synthetic when examining what synthetic research can provide for architectural discourse. Synthesis contrasts with analysis in that its primary method involves recourse to experience; it is experience that is at the heart of synthetic research. The synthesis of theory, architectural constructions, and digital techniques requires experiencing the results of experimentation. Synthetic digital architecture necessitates a discovery process incorporating creation that allows for experience, be it virtual reality, full-scale proto-typing or spatial creations; provided experience is a truthful one, and not disingenuous, slipping into the alternate definition of synthetic.