Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA014208
PROPERTIES
| NPAID | NPA014208 |
|---|---|
| CLUSTER ID | 180 |
| NODE ID | 168 |
| NAME | Spirotryprostatin B |
| FORMULA | C21H21N3O3 |
| MOLECULAR WEIGHT (Da) | 363.4170 |
| ACCURATE MASS (Da) | 363.1583 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Aspergillus |
| ORIGIN SPECIES | fumigatus |
| InChIKey | IWUYVKKHPNFWJG-WJPUGNRLSA-N |
| InChI | InChI=1S/C21H21N3O3/c1-12(2)10-17-21(13-6-3-4-7-14(13)22-20(21)27)11-16-18(25)23-9-5-8-15(23)19(26)24(16)17/h3-4,6-7,10-11,15,17H,5,8-9H2,1-2H3,(H,22,27)/t15-,17-,21-/m0/s1 |
| SMILES | CC(=C[C@H]1[C@]2(C=C3N1C(=O)[C@@H]4CCCN4C3=O)C5=CC=CC=C5NC2=O)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | CUI, CHENG-BIN; KAKEYA, HIDEAKI; OSADA, HIROYUKI Spirotryprostatin B, a Novel Mammalian Cell Cycle Inhibitor Produced by Aspergillus fumigatus Journal of Antibiotics 1996 49 (8) 832-835. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.49.832 | PMID | 8823522 |
SYNTHESES
| CITATION 1 | von Nussbaum F; Danishefsky SJ A Rapid Total Synthesis of Spirotryprostatin B: Proof of Its Relative and Absolute Stereochemistry F.v.N. gratefully acknowledges the Alexander-von-Humboldt-Stiftung for a Feodor-Lynen fellowship that was kindly backed by Dr. R. Breslow as second host. This research was supported by the National Institutes of Health (Grant number HL 25848). We thank Dr. H. Osada (RIKEN) for providing us with spectra of the natural product. Furthermore we are grateful to Dr. D. Lichtblau from the Nakanishi laboratory for help with the CD spectra. We acknowledge the collaborative efforts of Ms. Maria Manzoni in these studies. Angewandte Chemie International Edition 2000 39 (12) 2175-2178. DOI: 10.1002/1521-3773(20000616)39:12<2175::AID-ANIE2175>3.0.CO;2-J PMID: 10941053 | ||
|---|---|---|---|
| CITATION 2 | Wang H; Ganesan A A biomimetic total synthesis of (-)-spirotryprostatin B and related studies. Journal of Organic Chemistry 2000 65 (15) 4685-93. DOI: 10.1021/jo000306o PMID: 10959875 | ||
| CITATION 3 | Bagul TD; Lakshmaiah G; Kawabata T; Fuji K Total synthesis of spirotryprostatin B via asymmetric nitroolefination. Organic Letters 2002 4 (2) 249-51. DOI: 10.1021/ol016999s PMID: 11796062 | ||
| CITATION 4 | Meyers C; Carreira EM Total synthesis of (-)-spirotryprostatin B. Angewandte Chemie International Edition 2003 42 (6) 694-6. DOI: 10.1002/anie.200390192 PMID: 12575009 | ||
| CITATION 5 | Marti C; Carreira EM Total synthesis of (-)-spirotryprostatin B: synthesis and related studies. Journal of the American Chemical Society 2005 127 (32) 11505-15. DOI: 10.1021/ja0518880 PMID: 16089481 | ||
| CITATION 6 | Trost BM; Stiles DT Total synthesis of spirotryprostatin B via diastereoselective prenylation. Organic Letters 2007 9 (15) 2763-6. DOI: 10.1021/ol070971k PMID: 17592853 | ||
