A Pericyclic Reaction Cascade in Leporin Biosynthesis | Zendy

Glöckle Anna | Zendy; Gulder Tobias A. M. | Zendy

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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.

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