Synthesis and Structure Elucidation of Tedanolide C

• Applicant: Professor Dr. Markus Kalesse
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2017 to 2022
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 397946801

This projects aims at the total synthesis of tedanolide C. Tedanolid C exhibits, compared to the other tedanolides, a much higher oxidation pattern which leads to a tertiary hydroxyl group next to a primary alcohol. These features represent a particular synthetic challenge for the construction of this very fragment but also for the assembly of all building blocks. We developed a variation of the Kiyooka aldol reaction, which was used by us for the generation of this complex fragment. Within this proposal we delineate how tedanolide C can be constructed using our Kiyooka aldol approach. A total synthesis of tedanolide C would have significance since several groups question the proposed configuration and a successful total synthesis would confirm one or the other structural proposal. Tedanolide C as well as the whole family of tedanolides represent an important class of natural products as they address to distinct binding sites at the ribosome and belong to one of the most cytotoxic natural products. The fact that these are marine natural products disables access through fermentation and makes a synthetic access even more important.

• DFG Programme: Research Grants