A Pericyclic Reaction Cascade in Leporin Biosynthesis

Angew. Chem. Int. Ed., Volume 57, Issue 11, Pages 2754-2756, DOI: 10.1002/anie.201800629
Angew. Chem. Int. Ed., online article

All roads lead to Rome: The biosynthesis of the leporins in Aspergillus sp. involves an unprecedented pericyclic reaction cascade. The enzyme LepI directs the periselectivity of a [4+2] cycloaddition towards a hetero‐Diels–Alder reaction outcome to give the leporin molecular scaffold. The Diels–Alder side product is morphed into the leporin core structure by a LepI‐catalyzed retro‐Claisen rearrangement, culminating in efficient kinetic side product recycling.
 

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