Total synthesis and biological evaluation of C-nor-D-homo Steroids

• Applicant: Professor Dr. Athanassios Giannis
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2014 to 2018
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 268346890

C-nor-D-homo steroids (6-6-5-6 annulated systems) are natural products with interesting biological properties ranging from anti-tumoral to anti-diabetic activities. Despite of their importance in biology and medicine only a few synthetic entries to this steroids were described in the literature. In the frame of this proposal a general entry will be established. Starting from (-)-citronellal and the readily available (+)-Wieland-Miescher ketone, in a convergent approach, an open chain precursor will be synthesized which in a subsequent reaction, using the Nazarov cyclisation as a key step, will be transformed in one step to the C-nor-D-homo steroid. Our efforts will open the way to a general entry to this class of steroids and their non natural analogs. The synthesized compounds will be biologically evaluated using the Gli-reporter assay.

• DFG Programme: Research Grants