Synthesis of a sugar

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Abstract

The goal of my work placement was to synthesize the 6-C-arabinopyranosylapigenin which is a flavonoid compound.
It is a putative biosynthetic product from the plant Desmodium uncinatum.
This plant is used, on the one hand, to repel moths which attack Kenya's maize plant, but also to eliminate the parasitic weed Striga hermonthica. The C-glucosyle flavonoids arereally active in the elimination of the parasitic weed.
This compound could be a good reference to find the same type of product into the Desmodium's roots and to be able to create a molecule which send a chemical signal (or semiochemical) to Striga and destroy it without environmental impact.
The products until the C-glycosyl compound were synthesized.

Résumé
Le but demon stage était de synthétiser le 6-C-arabinopyranosylapigénine qui est un flavonoïde.
Ce composé provient d'une plante nommée Desmodium uncinatum. Cette plante est utilisée au Kenya pour repousser les insectes qui ravagent les champs de maïs d'une part, mais aussi pour éliminer la plante parasite Striga hermonthica. Les flavonoïdes C-glucosylés sont actifs dans l'élimination de laplante parasite.
Cette molécule pourra servir de référence pour identifier un produit de même type dans les racines du Desmodium. A terme, ce flavonoïde pourrait envoyer un signal chimique au Striga, détruisant cette plante parasite sans être néfaste pour l'environnement.
Les produits jusqu'au composé C-glycosylé ont pu être synthétisés.

Acknowledgments

I wish to addressacknowledgment to the following persons:

- My supervisor Dr Tony Hooper for his patience, for the knowledge he passed on to me during my training placement.

- Dr Patrick Mayon for helping me during this work placement.

- The regional council of the Centre Region of France which helped me a lot e financially.

- The staff of BCH department.

- The manorfamily with whom I spent some very good moments.

Summary

➢ Abstract..................................................................................................................2
➢ Abbreviation list......................................................................................................5
➢Introduction.............................................................................................................6
I. Presentation of Rothamsted Research Limited................................................7
a. History of Rothamsted Research...........................................................7
b. Department............................................................................................8
I. Presentation of thesubject.............................................................................10
a. Kenya and the problems of African crops............................................10
b. Enemy of maize..................................................................................10
c. The Push-Pulltechnology....................................................................12
d. Why synthesise 6-C-arabinopyranosylapigenin?.................................13
II. Synthesis of the compound.............................................................................15
a. Preparation of arabinose......................................................................16
b. Preparation of2,4,6-trihydroxyacetophenone......................................20
c. Rearrangement....................................................................................24
III. Experimental result.........................................................................................25
➢ Scientific conclusion.............................................................................................30
➢ Personal...
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