Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA019655
PROPERTIES
| NPAID | NPA019655 |
|---|---|
| CLUSTER ID | 6303 |
| NODE ID | 4373 |
| NAME | Gliocladin C |
| FORMULA | C22H16N4O3 |
| MOLECULAR WEIGHT (Da) | 384.3950 |
| ACCURATE MASS (Da) | 384.1222 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Gliocladium |
| ORIGIN SPECIES | catenulatum |
| InChIKey | ZGZLUDDEYVIROA-FGZHOGPDSA-N |
| InChI | InChI=1S/C22H16N4O3/c1-25-18(27)17-10-22(14-11-23-15-8-4-2-6-12(14)15)13-7-3-5-9-16(13)24-21(22)26(17)20(29)19(25)28/h2-11,21,23-24H,1H3/t21-,22-/m1/s1 |
| SMILES | CN1C(=O)C2=C[C@]3([C@@H](N2C(=O)C1=O)NC4=CC=CC=C43)C5=CNC6=CC=CC=C65 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Bertinetti, Brenda V; Rodriguez, M Alejandra; Godeas, Alicia M; Cabrera, Gabriela M 1H,1'H-[3,3']biindolyl from the terrestrial fungus Gliocladium catenulatum Journal of Antibiotics 2010 63 (11) 681-683. | ||
|---|---|---|---|
| DOI | 10.1038/ja.2010.103 | PMID | 20823893 |
SYNTHESES
| CITATION 1 | Overman LE; Shin Y Enantioselective total synthesis of (+)-gliocladin C. Organic Letters 2007 9 (2) 339-41. DOI: 10.1021/ol062801y PMID: 17217299 | ||
|---|---|---|---|
| CITATION 2 | Song J; Guo C; Adele A; Yin H; Gong LZ Enantioselective organocatalytic construction of hexahydropyrroloindole by means of α-alkylation of aldehydes leading to the total synthesis of (+)-gliocladin C. Chemistry - A European Journal 2013 19 (10) 3319-23. DOI: 10.1002/chem.201204522 PMID: 23401076 | ||
| CITATION 3 | Tayu M; Hui Y; Takeda S; Higuchi K; Saito N; Kawasaki T Total Synthesis of (+)-Gliocladin C Based on One-Pot Construction of a 3a-(3-Indolyl)pyrroloindoline Skeleton by Sulfonium-Mediated Cross-Coupling of Tryptophan and Indole. Organic Letters 2017 19 (24) 6582-6585. DOI: 10.1021/acs.orglett.7b03293 PMID: 29205043 | ||
