Roseophilin

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
CAS Registry Number	142386-38-7
ChEMBL	ChEMBL1945189
ChemSpider	4578301 Y
InChI InChI=1S/C27H33ClN2O2/c1-16(2)23-18-11-9-7-5-4-6-8-10-17-14-19(23)25(30-17)24(18)27-22(31-3)15-21(32-27)26-20(28)12-13-29-26/h12-16,18,23,30H,4-11H2,1-3H3/b26-21-,27-24- Y Key: XEQIXGXEBJYNMG-OLPWBVPVSA-N Y InChI=1/C27H33ClN2O2/c1-16(2)23-18-11-9-7-5-4-6-8-10-17-14-19(23)25(30-17)24(18)27-22(31-3)15-21(32-27)26-20(28)12-13-29-26/h12-16,18,23,30H,4-11H2,1-3H3/b26-21-,27-24- Key: XEQIXGXEBJYNMG-OLPWBVPVBQ
Jmol-3D images	Image
PubChem	5467324
SMILES Cl\C\5=C\C=N/C/5=C4\O/C(=C2\c1nc3cc1C(C(C)C)C2CCCCCCCC3)/C(/OC)=C4
Properties
Chemical formula	C27H33ClN2O2
Molar mass	453.02 g/mol
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

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, Furstner, Salamone) are based upon the Paal-Knorr synthesis, and two others are based on the Nazarov cyclization reaction (those of Tius, Frontier).

References