Asymmetric Synthesis and Biosynthetic Implications of (+)-Fusarisetin A

Asymmetric Synthesis and Biosynthetic Implications of (+)-Fusarisetin A

Starting from equisetin, the asymmetric synthesis of (+)‐fusarisetin A has been accomplished in a one‐pot transformation including a biomimetic oxidation and an intramolecular Diels–Alder/Roskamp reaction. Peroxyfusarisetin is proposed as a plausible biosynthetic intermediate based on studies of the...

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Veröffentlicht in:Angewandte Chemie International Edition 2012-07, Vol.51 (31), p.7786-7789
Hauptverfasser: Yin, Jun, Wang, Cheng, Kong, Lili, Cai, Shujun, Gao, Shuanhu
Format: Artikel
Sprache:eng
Schlagworte:
biosynthesis
Heterocyclic Compounds, 4 or More Rings - chemical synthesis
Heterocyclic Compounds, 4 or More Rings - chemistry
Heterocyclic Compounds, 4 or More Rings - metabolism
Molecular Conformation
natural products
peroxides
radical reactions
Stereoisomerism
total synthesis
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Zusammenfassung:Starting from equisetin, the asymmetric synthesis of (+)‐fusarisetin A has been accomplished in a one‐pot transformation including a biomimetic oxidation and an intramolecular Diels–Alder/Roskamp reaction. Peroxyfusarisetin is proposed as a plausible biosynthetic intermediate based on studies of the oxidation of equisetin.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201202455