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

Research output: Contribution to journalArticle

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 languageEnglish (US)
Pages (from-to)7835-7838
Number of pages4
JournalAngewandte Chemie - International Edition
Volume45
Issue number46
DOIs
StatePublished - Nov 27 2006

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Pyrones
Polyketides
Polyenes
Propionates
Immunosuppressive Agents
SNF 4435C
orinocin
spectinabilin
mesitylene
Hot Temperature

Keywords

  • Electrocyclic reactions
  • Natural products
  • Polyenes
  • Polyketides
  • Streptomyces

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Photochemical origin of the immunosuppressive SNF4435C/D and formation of orinocin through "polyene splicing". / Müller, Markus; Kusebauch, Björn; Liang, Guangxin; Beaudry, Christopher M.; Trauner, Dirk; Hertweck, Christian.

In: Angewandte Chemie - International Edition, Vol. 45, No. 46, 27.11.2006, p. 7835-7838.

Research output: Contribution to journalArticle

Müller, Markus ; Kusebauch, Björn ; Liang, Guangxin ; Beaudry, Christopher M. ; Trauner, Dirk ; Hertweck, Christian. / Photochemical origin of the immunosuppressive SNF4435C/D and formation of orinocin through "polyene splicing". In: Angewandte Chemie - International Edition. 2006 ; Vol. 45, No. 46. pp. 7835-7838.
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