Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA007977
PROPERTIES
| NPAID | NPA007977 |
|---|---|
| CLUSTER ID | 3481 |
| NODE ID | 650 |
| NAME | Cycloclavine |
| FORMULA | C16H18N2 |
| MOLECULAR WEIGHT (Da) | 238.3340 |
| ACCURATE MASS (Da) | 238.1470 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Aspergillus |
| ORIGIN SPECIES | jaonicus SAITO IFO 4060 |
| InChIKey | ZWJHDICNUKHUGE-FVQBIDKESA-N |
| InChI | InChI=1S/C16H18N2/c1-15-8-16(15)11-4-3-5-12-14(11)10(7-17-12)6-13(16)18(2)9-15/h3-5,7,13,17H,6,8-9H2,1-2H3/t13-,15-,16-/m1/s1 |
| SMILES | C[C@]12C[C@@]13[C@@H](CC4=CNC5=CC=CC3=C45)N(C2)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Furuta, Takaki; Koike, Masami; Abe, Matazo Isolation of Cycloclavine from the Culture Broth of Aspergillus japonicus SAITO Agricultural and Biological Chemistry 1982 46 (7) 1921-1922. | ||
|---|---|---|---|
| DOI | 10.1080/00021369.1982.10865353 | PMID | - |
SYNTHESES
| CITATION 1 | Petronijevic FR; Wipf P Total synthesis of (±)-cycloclavine and (±)-5-epi-cycloclavine. Journal of the American Chemical Society 2011 133 (20) 7704-7. DOI: 10.1021/ja2026882 PMID: 21517102 | ||
|---|---|---|---|
| CITATION 2 | Jabre ND; Watanabe T; Brewer M Formal and total synthesis of (±)-cycloclavine. Tetrahedron Letters 2014 56 (1) 197-199. DOI: 10.1016/j.tetlet.2013.10.152 PMID: 24511164 | ||
| CITATION 3 | Netz N; Opatz T A Modular Formal Total Synthesis of (±)-Cycloclavine. Journal of Organic Chemistry 2016 81 (4) 1723-30. DOI: 10.1021/acs.joc.5b02815 PMID: 26811951 | ||
| CITATION 4 | McCabe SR; Wipf P Eight-Step Enantioselective Total Synthesis of (-)-Cycloclavine. Angewandte Chemie International Edition 2017 56 (1) 324-327. DOI: 10.1002/anie.201608820 PMID: 27860203 | ||
| CITATION 5 | Chaudhuri S; Ghosh S; Bhunia S; Bisai A Catalytic asymmetric formal total syntheses of (+)- and (-)-cycloclavine. Chemical Communications 2018 54 (8) 940-943. DOI: 10.1039/c7cc09045e PMID: 29318233 | ||
| CITATION 6 | Deng L; Chen M; Dong G Concise Synthesis of (-)-Cycloclavine and (-)-5- epi-Cycloclavine via Asymmetric C-C Activation. Journal of the American Chemical Society 2018 140 (30) 9652-9658. DOI: 10.1021/jacs.8b05549 PMID: 29976068 | ||
