Photochemical origin of the immunosuppressive SNF4435C/D and formation of orinocin through "polyene splicing"

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

doi:10.1002/anie.200602840

Photochemical origin of the immunosuppressive SNF4435C/D and formation of orinocin through "polyene splicing"

Markus Müller, Björn Kusebauch, Guangxin Liang, Christopher M. Beaudry, Dirk Trauner, Christian Hertweck

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

(Chemical Equation Presented). 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).

Original language	English (US)
Pages (from-to)	7835-7838
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	45
Issue number	46
DOIs	https://doi.org/10.1002/anie.200602840
State	Published - Nov 27 2006

Keywords

Electrocyclic reactions
Natural products
Polyenes
Polyketides
Streptomyces

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200602840

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AU - Liang, Guangxin

AU - Beaudry, Christopher M.

AU - Trauner, Dirk

AU - Hertweck, Christian

PY - 2006/11/27

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AB - (Chemical Equation Presented). 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).

KW - Electrocyclic reactions

KW - Natural products

KW - Polyenes

KW - Polyketides

KW - Streptomyces

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Photochemical origin of the immunosuppressive SNF4435C/D and formation of orinocin through "polyene splicing"

Abstract

Keywords

ASJC Scopus subject areas

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