Roseophilin
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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 | |
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Chemical formula | 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). ![]() ![]() ![]() Infobox references |
Chemical compound
Roseophilin is an antibiotic isolated from Streptomyces griseoviridis 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). The compound is related to the prodiginines.[2]
References
- ^ Fürstner, A. (2003). "Chemistry and Biology of Roseophilin and the Prodigiosin Alkaloids: A Survey of the Last 2500 Years". Angew. Chem. Int. Ed. 42 (31): 3582–3603. doi:10.1002/anie.200300582. PMID 12916029.
- ^ Hu, Dennis X.; Withall, David M.; Challis, Gregory L.; Thomson, Regan J. (2016). "Structure, Chemical Synthesis, and Biosynthesis of Prodiginine Natural Products". Chemical Reviews. 116 (14): 7818–7853. doi:10.1021/acs.chemrev.6b00024. PMC 5555159. PMID 27314508.
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