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A Pericyclic Reaction Cascade in Leporin Biosynthesis
Author(s) -
Glöckle Anna,
Gulder Tobias A. M.
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201800629
Subject(s) - pericyclic reaction , cycloaddition , biosynthesis , cascade reaction , chemistry , cascade , stereochemistry , natural product , combinatorial chemistry , enzyme , organic chemistry , catalysis , chromatography
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.