UMR 5182

logo-ensl

Hemicryptophanes Synthesis

We develop the synthesis of new hemicryptophane cage compounds with various size, shape and functionalities inside the cavity. Moreover, large scale syntheses of these host molecules are also performed.

 

We develop the synthesis of new hemicryptophane cage compounds with various size, shape and functionalities inside the cavity. Moreover, large scale syntheses of these host molecules are also performed.

new_hemi1.png

 

Hemicryptophanes derived from tris(N-alkyl-carbamoylmethyl)amine and tris(2-aminoethyl)amine (tren) have been synthesized following a single synthetic pathway.

new_hemi2.png

 

Hemicryptophane was synthesized at the gram scale in four steps from vanillyl alcohol compared to the previous seven-step procedure. The size, shape, and functionalities of the molecular cavity were also easily modified.

 

 

Persons involved: Bastien Chatelet, Oliver Perraud, Aline Schmitt, Laure-lise Chapellet, Lionel Joucla, Alexandre Martinez, Jean-Pierre Dutasta

 

Related Publications:

1. “Shorter and Modular Synthesis of Hemicryptophane-tren Derivatives” B. Chatelet, E. Payet, O. Perraud, P. Dimitrov-Raytchev, L.-C. Chapellet, V. Dufaud, A. Martinez, J.-P. Dutasta, Org. Lett. 2011, 13, 3706.

2. “A New Class of C3-Symmetrical Hemicryptophane Hosts: Triamide- and Tren-Hemicryptophanes” P. Dimitrov Raytchev, O. Perraud, C. Aronica, A. Martinez, J.-P. Dutasta, J. Org. Chem. 2010, 75, 2099.