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

• Final Report Year: 2018

Final Report Abstract

A straightforward synthesis of C-nor-D-homo steroids starting from (+) Wieland–Miescher ketone wass accomplished and also reported. This convergent synthetic strategy utilizes a scalable diastereoselective Nazarov cyclization of functionalized chiral aryl vinyl ketones, allowing for further functionalization. The ability to conduct this key transformation on a multi-gram scale paves the way for the synthesis of a variety of completely new C-nor-D-homo steroids, without the need of a classic steran steroid rearrangement or achiral linear reaction sequences.

Publications

• 2018. “Synthesis of C-Nor-D-homo-steroidal Alkaloids and Their Derivatives”
  F. Mousavizadeh, D. Meyer, A. Giannis, Synthesis
  (See online at https://dx.doi.org/10.1055/s-0036-1591965)
• Chem. Eur. J. 2017, 23, 5000 - 5004. "Lewis Acid Mediated Nazarov Cyclization as a Convergent and Enantioselective Entry to C-nor-D-homo-Steroids."
  J. Krieger, T. Smeilus, O. Schackow, A. Giannis
  (See online at https://doi.org/10.1002/chem.201701008)