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Photochemical Origin of the Immunosuppressive SNF4435C/D and Formation of Orinocin through “Polyene Splicing”
Author(s) -
Müller Markus,
Kusebauch Björn,
Liang Guangxin,
Beaudry Christopher M.,
Trauner Dirk,
Hertweck Christian
Publication year - 2006
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.200602840
Subject(s) - polyene , chemistry , pericyclic reaction , photochemistry , mesitylene , stereochemistry , organic chemistry , benzene
A splice from life : A photoinduced rearrangement cascade with alternating photochemical and thermal pericyclic steps leads to a novel pyrone compound with chain‐contracted polyketide backbone (orinocin ( 2 )). The excision of three propionate units from the polyene precursor, spectinabilin ( 1 ), proceeds via the immunosuppressive SNF4435C/D and yields an unusual triketide, mesitylene (see scheme).