Efficient total synthesis of leiodermatolide

• Applicant: Dr. Julian Wippich
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: Funded in 2017
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 372789477

• Final Report Year: 2017

Final Report Abstract

The initially proposed route of the western fragment of leiodermatolide failed due to the problematic coupling of the homo zinc enolate with the vinyl bromide 12. After revising the retrosynthetic route for several more time, we were able to complete the western fragment employing a diastereoselective Sakurai reaction. Finally, the eastern and western fragment were joined by a esterification. The remaining main challenge is now to close the lactone ring in a Z-selective ring closing olefin metathesis. First experiments towards the desired product was not successful. The project will be continued in the Krische laboratory and the synthesis of the western fragment was recently accepted for publication.

Publications

• Org. Lett., 2017
  J. Roane, J. Wippich, S. D. Ramgren, M. J. Krische
  (See online at https://doi.org/10.1021/acs.orglett.7b03351)