Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA006796
PROPERTIES
| NPAID | NPA006796 |
|---|---|
| CLUSTER ID | 71 |
| NODE ID | 66 |
| NAME | Communesin F |
| FORMULA | C28H32N4O |
| MOLECULAR WEIGHT (Da) | 440.5910 |
| ACCURATE MASS (Da) | 440.2576 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Penicillium |
| ORIGIN SPECIES | expansum Link MK-57 |
| InChIKey | AJKLOOXVDIANRY-MGDFUXISSA-N |
| InChI | InChI=1S/C28H32N4O/c1-17(2)16-23-19-8-7-11-22-24(19)28-13-15-32(23)26-27(28,12-14-31(26)18(3)33)20-9-5-6-10-21(20)29-25(28)30(22)4/h5-11,16,23,25-26,29H,12-15H2,1-4H3/t23-,25-,26-,27+,28+/m1/s1 |
| SMILES | CC(=C[C@@H]1C2=C3C(=CC=C2)N([C@@H]4[C@]35CCN1[C@@H]6[C@]5(CCN6C(=O)C)C7=CC=CC=C7N4)C)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Hayashi, Hideo; Matsumoto, Hirotaka; Akiyama, Kohki New Insecticidal Compounds, Communesins C, D and E, from Penicillium expansum Link MK-57 Bioscience Biotechnology and Biochemistry 2004 68 (3) 753-756. | ||
|---|---|---|---|
| DOI | 10.1271/bbb.68.753 | PMID | 15056914 |
SYNTHESES
| CITATION 1 | Yang J; Wu H; Shen L; Qin Y Total synthesis of (+/-)-communesin F. Journal of the American Chemical Society 2007 129 (45) 13794-5. DOI: 10.1021/ja075705g PMID: 17956099 | ||
|---|---|---|---|
| CITATION 2 | Liu P; Seo JH; Weinreb SM Total synthesis of the polycyclic fungal metabolite (+/-)-communesin F. Angewandte Chemie International Edition 2010 49 (11) 2000-3. DOI: 10.1002/anie.200906818 PMID: 20175174 | ||
| CITATION 3 | Zuo Z; Xie W; Ma D Total synthesis and absolute stereochemical assignment of (-)-communesin F. Journal of the American Chemical Society 2010 132 (38) 13226-8. DOI: 10.1021/ja106739g PMID: 20812683 | ||
| CITATION 4 | Belmar J; Funk RL Total synthesis of (±)-communesin F via a cycloaddition with indol-2-one. Journal of the American Chemical Society 2012 134 (41) 16941-3. DOI: 10.1021/ja307277w PMID: 22978807 | ||
| CITATION 5 | Lathrop SP; Pompeo M; Chang WT; Movassaghi M Convergent and Biomimetic Enantioselective Total Synthesis of (-)-Communesin F. Journal of the American Chemical Society 2016 138 (24) 7763-9. DOI: 10.1021/jacs.6b04072 PMID: 27244250 | ||
| CITATION 6 | Liang X; Zhang TY; Zeng XY; Zheng Y; Wei K; Yang YR Ir-Catalyzed Asymmetric Total Synthesis of (-)-Communesin F. Journal of the American Chemical Society 2017 139 (9) 3364-3367. DOI: 10.1021/jacs.7b00854 PMID: 28219006 | ||
| CITATION 7 | Park J; Jean A; Chen DY Asymmetric Total Syntheses of Communesin F and a Putative Member of the Communesin Family. Angewandte Chemie International Edition 2017 56 (45) 14237-14240. DOI: 10.1002/anie.201707806 PMID: 28926206 | ||
