Compounds
COMPOUND NPA009289
PROPERTIES
| NPAID | NPA009289 |
|---|---|
| CLUSTER ID | 3870 |
| NODE ID | 2898 |
| NAME | Podophyllotoxin |
| FORMULA | C22H22O8 |
| MOLECULAR WEIGHT (Da) | 414.4100 |
| ACCURATE MASS (Da) | 414.1315 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Phialocephala |
| ORIGIN SPECIES | fortinii |
| InChIKey | YJGVMLPVUAXIQN-XVVDYKMHSA-N |
| InChI | InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1 |
| SMILES | COC1=CC(=CC(=C1OC)OC)[C@H]2[C@@H]3[C@H](COC3=O)[C@H](C4=CC5=C(C=C24)OCO5)O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Eyberger, Amy L.; Dondapati, Rajeswari; Porter, John R. Endophyte fungal isolates from Podophyllum peltatum produce podophyllotoxin Journal of Natural Products 2006 69 (8) 1121-1124. | ||
|---|---|---|---|
| DOI | 10.1021/np060174f | PMID | 16933860 |
SYNTHESES
| CITATION 1 | Ting CP; Maimone TJ C-H bond arylation in the synthesis of aryltetralin lignans: a short total synthesis of podophyllotoxin. Angewandte Chemie International Edition 2014 53 (12) 3115-3119. DOI: 10.1002/anie.201311112 PMID: 24519950 | ||
|---|---|---|---|
| CITATION 2 | Wu Y; Zhang H; Zhao Y; Zhao J; Chen J; Li L A new and efficient strategy for the synthesis of podophyllotoxin and its analogues. Organic Letters 2007 9 (7) 1199-1202. DOI: 10.1021/ol0630954 PMID: 17326644 | ||
| CITATION 3 | Wu Y; Zhao J; Chen J; Pan C; Li L; Zhang H Enantioselective sequential conjugate addition-allylation reactions: a concise total synthesis of (+)-podophyllotoxin. Organic Letters 2009 11 (3) 597-600. DOI: 10.1021/ol8026208 PMID: 19105659 | ||
| CITATION 4 | Berkowitz DB; Choi S; Maeng JH Enzyme-assisted asymmetric total synthesis of (-)-podophyllotoxin and (-)-picropodophyllin. Journal of Organic Chemistry 2000 65 (3) 847-860. DOI: 10.1021/jo991582+ PMID: 10814019 | ||
| CITATION 5 | Hajra S; Garai S; Hazra S Catalytic Enantioselective Synthesis of (-)-Podophyllotoxin. Organic Letters 2017 19 (24) 6530-6533. DOI: 10.1021/acs.orglett.7b03236 PMID: 29210277 | ||
| CITATION 6 | Casey M; Keaveney CM A concise stereocontrolled formal total synthesis of (+/-)-podophyllotoxin using sulfoxide chemistry. Chemical Communications 2004 (2) 184-185. DOI: 10.1039/b312245j PMID: 14737540 | ||
| CITATION 7 | Lazzarotto M; Hammerer L; Hetmann M; Borg A; Schmermund L; Steiner L; Hartmann P; Belaj F; Kroutil W; Gruber K; Fuchs M Chemoenzymatic Total Synthesis of Deoxy-, epi-, and Podophyllotoxin and a Biocatalytic Kinetic Resolution of Dibenzylbutyrolactones. Angewandte Chemie International Edition 2019 58 (24) 8226-8230. DOI: 10.1002/anie.201900926 PMID: 30920120 | ||
| CITATION 8 | Li J; Zhang X; Renata H Asymmetric Chemoenzymatic Synthesis of (-)-Podophyllotoxin and Related Aryltetralin Lignans. Angewandte Chemie International Edition 2019 58 (34) 11657-11660. DOI: 10.1002/anie.201904102 PMID: 31241812 | ||
