Photochemical Origin of the Immunosuppressive SNF4435C/D and Formation of Orinocin through “Polyene Splicing” | Zendy

Müller Markus | Zendy; Kusebauch Björn | Zendy; Liang Guangxin | Zendy; Beaudry Christopher M. | Zendy; Trauner Dirk | Zendy; Hertweck Christian | Zendy

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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).

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