Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA008347
PROPERTIES
| NPAID | NPA008347 |
|---|---|
| CLUSTER ID | 17 |
| NODE ID | 17 |
| NAME | Paspaline |
| FORMULA | C28H39NO2 |
| MOLECULAR WEIGHT (Da) | 421.6250 |
| ACCURATE MASS (Da) | 421.2981 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Claviceps |
| ORIGIN SPECIES | paspali |
| InChIKey | WLAIEIMDXUAGPY-HSECPPETSA-N |
| InChI | InChI=1S/C28H39NO2/c1-25(2,30)22-12-14-26(3)21-11-10-17-16-19-18-8-6-7-9-20(18)29-24(19)28(17,5)27(21,4)15-13-23(26)31-22/h6-9,17,21-23,29-30H,10-16H2,1-5H3/t17-,21-,22-,23-,26-,27-,28+/m0/s1 |
| SMILES | C[C@@]12CC[C@H](O[C@H]1CC[C@]3([C@H]2CC[C@@H]4[C@@]3(C5=C(C4)C6=CC=CC=C6N5)C)C)C(C)(C)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Springer, James P; Clardy, Jon; others Paspaline and paspalicine, two indole-mevalonate metabolites from Claviceps paspali Tetrahedron Letters 1980 21 (3) 231-234. | ||
|---|---|---|---|
| DOI | 10.1016/s0040-4039(00)71176-2 | PMID | - |
SYNTHESES
| CITATION 1 | Sharpe RJ; Johnson JS A global and local desymmetrization approach to the synthesis of steroidal alkaloids: stereocontrolled total synthesis of paspaline. Journal of the American Chemical Society 2015 137 (15) 4968-71. DOI: 10.1021/jacs.5b02631 PMID: 25856767 | ||
|---|---|---|---|
| CITATION 2 | Sharpe RJ; Johnson JS Asymmetric Total Synthesis of the Indole Diterpene Alkaloid Paspaline. Journal of Organic Chemistry 2015 80 (19) 9740-66. DOI: 10.1021/acs.joc.5b01844 PMID: 26398568 | ||
| CITATION 3 | Kim DE; Zweig JE; Newhouse TR Total Synthesis of Paspaline A and Emindole PB Enabled by Computational Augmentation of a Transform-Guided Retrosynthetic Strategy. Journal of the American Chemical Society 2019 141 (4) 1479-1483. DOI: 10.1021/jacs.8b13127 PMID: 30626183 | ||
