Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA002965
PROPERTIES
| NPAID | NPA002965 |
|---|---|
| CLUSTER ID | 1704 |
| NODE ID | 130 |
| NAME | Roseophilin |
| FORMULA | C27H33ClN2O2 |
| MOLECULAR WEIGHT (Da) | 453.0260 |
| ACCURATE MASS (Da) | 452.2231 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | griseoviridis 2464-S5 |
| InChIKey | AKRWVQHAEBBOTI-WZONZLPQSA-N |
| 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/h12-16,18,23,29H,4-11H2,1-3H3/t18-,23-/m1/s1 |
| SMILES | CC(C)[C@@H]1[C@H]2CCCCCCCCC3=NC(=C2C4=C(C=C(O4)C5=C(C=CN5)Cl)OC)C1=C3 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Hayakawa, Yoichi; Kawakami, Kenji; Seto, Haruo; Furihata, Kazuo Structure of a new antibiotic, roseophilin Tetrahedron Letters 1992 33 (19) 2701-2704. | ||
|---|---|---|---|
| DOI | 10.1016/s0040-4039(00)79061-7 | PMID | - |
SYNTHESES
| CITATION 1 | Harrington PE; Tius MA Synthesis and absolute stereochemistry of roseophilin. Journal of the American Chemical Society 2001 123 (35) 8509-8514. DOI: 10.1021/ja011242h PMID: 11525658 | ||
|---|---|---|---|
| CITATION 2 | Bamford SJ; Luker T; Speckamp WN; Hiemstra H Enantioselective formal total synthesis of roseophilin. Organic Letters 2000 2 (8) 1157-1160. DOI: 10.1021/ol005750s PMID: 10804578 | ||
| CITATION 3 | Harrington PE; Tius MA A formal total synthesis of roseophilin: cyclopentannelation approach to the macrocyclic core. Organic Letters 1999 1 (4) 649-651. DOI: 10.1021/ol990124k PMID: 10823195 | ||
| CITATION 4 | Frederich JH; Harran PG Modular access to complex prodiginines: total synthesis of (+)-roseophilin via its 2-azafulvene prototropisomer. Journal of the American Chemical Society 2013 135 (10) 3788-3791. DOI: 10.1021/ja400473v PMID: 23452332 | ||
| CITATION 5 | Zhang X; Zhang C; Wang X; Liang G Mild Friedel-Crafts Reactions Enable a Robust Synthesis of Roseophilin. Organic Letters 2019 21 (9) 3357-3360. DOI: 10.1021/acs.orglett.9b01100 PMID: 31008613 | ||
