Roseophilin

Roseophilin is an antibiotic isolated from Streptomyces griscovirides shown to have antitumor activity.[1] The chemical structure can be considered in terms of two components, a macrotricyclic segment and a heterocyclic side-chain. Several laboratory syntheses of roseophilin (e.g., those of Trost, Fürstner, Salamone) are based upon the Paal-Knorr synthesis, and two others are based on the Nazarov cyclization reaction (those of Tius, Frontier).

Roseophilin
Names
IUPAC name
15-[5-(3-Chloro-1H-pyrrol-2-yl)-3-methoxy-furan-2-yl]-13-isopropyl-2-aza-tricyclo[10.2.1.13,14]hexadeca-1(15),2-triene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
Properties
C27H33ClN2O2
Molar mass 453.02 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

References

  1. Fürstner, A. (2003). "Chemistry and Biology of Roseophilin and the Prodigiosin Alkaloids: A Survey of the Last 2500 Years". Angew. Chem. Int. Ed. 42: 3582–3603. doi:10.1002/anie.200300582.


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