Compounds
COMPOUND NPA006965
PROPERTIES
| NPAID | NPA006965 |
|---|---|
| CLUSTER ID | 3170 |
| NODE ID | 2414 |
| NAME | Physostigmine |
| FORMULA | C15H21N3O2 |
| MOLECULAR WEIGHT (Da) | 275.3520 |
| ACCURATE MASS (Da) | 275.1634 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | sp. AH-4 |
| InChIKey | PIJVFDBKTWXHHD-HIFRSBDPSA-N |
| InChI | InChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1 |
| SMILES | C[C@@]12CCN([C@@H]1N(C3=C2C=C(C=C3)OC(=O)NC)C)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Murao, Sawao; Hayashi, Hideo Physostigmine and N8-norphysostigmine, insecticidal compounds, from Streptomyces sp Agricultural and Biological Chemistry 1986 50 (2) 523-524. | ||
|---|---|---|---|
| DOI | 10.1271/bbb1961.50.523 | PMID | - |
SYNTHESES
| CITATION 1 | Rege PD; Johnson F Application of vicarious nucleophilic substitution to the total synthesis of dl-physostigmine. Journal of Organic Chemistry 2003 68 (16) 6133-6139. DOI: 10.1021/jo026438u PMID: 12895041 | ||
|---|---|---|---|
| CITATION 2 | Pandey G; Khamrai J; Mishra A Generation of All-Carbon Quaternary Stereocenters at the C-3 Carbon of Lactams via [3,3]-Sigmatropic Rearrangement and Revision of Absolute Configuration: Total Synthesis of (-)-Physostigmine. Organic Letters 2018 20 (1) 166-169. DOI: 10.1021/acs.orglett.7b03537 PMID: 29272139 | ||
| CITATION 3 | Morales-Ríos MS; Santos-Sánchez NF; Joseph-Nathan P Efficient formal total synthesis of physostigmine and physovenine: conformational analysis of key intermediates. Journal of Natural Products 2002 65 (2) 136-141. DOI: 10.1021/np010475j PMID: 11858744 | ||
| CITATION 4 | Trost BM; Zhang Y Molybdenum-catalyzed asymmetric allylation of 3-alkyloxindoles: application to the formal total synthesis of (-)-physostigmine. Journal of the American Chemical Society 2006 128 (14) 4590-4591. DOI: 10.1021/ja060560j PMID: 16594693 | ||
| CITATION 5 | Kawahara M; Nishida A; Nakagawa M An efficient synthesis of optically active physostigmine from tryptophan via alkylative cyclization. Organic Letters 2000 2 (5) 675-678. DOI: 10.1021/ol005513p PMID: 10814407 | ||
| CITATION 6 | Pinto A; Jia Y; Neuville L; Zhu J Palladium-catalyzed enantioselective domino heck-cyanation sequence: development and application to the total synthesis of esermethole and physostigmine. Chemistry - A European Journal 2007 13 (3) 961-967. DOI: 10.1002/chem.200601016 PMID: 17009368 | ||
| CITATION 7 | Pandey G; Khamrai J; Mishra A Retraction of "An Expeditious Route to Both Enantiomers of All Carbon Quaternary Stereocenters at C-3 Carbon of Lactams via [3,3]-Sigmatropic Rearrangement: Total Synthesis of (-)-Physostigmine". Organic Letters 2017 19 (22) 6264. DOI: 10.1021/acs.orglett.7b03188 PMID: 29073764 | ||
