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Catalyst-controlled Divergent Synthesis of Aromatic Polyketides

Research Project
 | 
01.10.2017
 - 30.09.2021

The fascinating diversity of aromatic polyketides, which posses an impressive range of applications in medicine, can be traced to common linear poly-β-carbonyl precursors that are selectively folded and cyclized by a sophisticated biocatalytic machinery. It is therefore not surprising that chemists were captivated by the prospect of a biomimetic synthesis of aromatic polyketides since the beginnings of organic synthesis. However, due to the high reactivity systems and the manifold possibilities for cyclization reactions, these approaches have only allowed to study short poly-β-carbonyl systems without catalyst control. With the recent advances in catalysis, it is now within reach to mimic the controlled and selective folding of higher order poly-β-carbonyl with small-molecule catalysts. Inspired by the concepts of cyclic stereocontrol, the proposed strategy takes advantage of fewer conformational states, the lower number of folding modes and the developing ring strains in transannular aldol condensation of cyclic poly-β-carbonyl substrates. These substrates will be prepared by oxidative dissection of ambilaterally annulated hydroarene precursors. Treatment with suitable catalysts capable of controlling the folding mode will subsequently suture the polycyclic ring structure.

Funding

Catalyst-controlled Divergent Synthesis of Aromatic Polyketides

SNF Projekt (GrantsTool), 10.2017-09.2021 (48)
PI : Sparr, Christof.

Members (1)

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Christof Sparr

Principal Investigator