An improved preparation of phorbol from croton oil

Alberto Pagani, Simone Gaeta, Andrei I. Savchenko, Craig M. Williams and Giovanni Appendino
Beilstein J. Org. Chem. 2017, 13, 1361–1367. https://doi.org/10.3762/bjoc.13.133

Supporting Information

Supporting Information File 1: ESI-HRMS and 1H and 13C NMR spectra of compounds 1d and 1e.
Format: PDF Size: 2.8 MB Download

Cite the Following Article

An improved preparation of phorbol from croton oil
Alberto Pagani, Simone Gaeta, Andrei I. Savchenko, Craig M. Williams and Giovanni Appendino
Beilstein J. Org. Chem. 2017, 13, 1361–1367. https://doi.org/10.3762/bjoc.13.133

How to Cite

Pagani, A.; Gaeta, S.; Savchenko, A. I.; Williams, C. M.; Appendino, G. Beilstein J. Org. Chem. 2017, 13, 1361–1367. doi:10.3762/bjoc.13.133

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 794.6 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Mao, G.; Douglas, D.; Prajapati, M.; Janardhanam Raghavendra Rao, T.; Zheng, H.; Zhao, C.; Billack, B. Investigation of inflammatory mechanisms induced by croton oil in mouse ear. Current research in toxicology 2024, 7, 100184. doi:10.1016/j.crtox.2024.100184
  • Watanabe, A.; Hikone, Y.; Nagatomo, M.; Inoue, M. Conversion of Phorbol into Des-D-Ring Tricycle and Crotonianoid B via Peroxidation Reaction. Organic letters 2024, 26, 4335–4339. doi:10.1021/acs.orglett.4c01363
  • Maioli, C.; Amin, H. I. M.; Chianese, G.; Minassi, A.; Reddell, P. W.; Gaeta, S.; Taglialatela-Scafati, O.; Appendino, G. Novel Skeletal Rearrangements of the Tigliane Diterpenoid Core. Journal of natural products 2023, 86, 2685–2690. doi:10.1021/acs.jnatprod.3c00834
  • Fan, J.-P.; He, B.-T.; Gao, Y.; Xie, C.-F.; Chen, H.-P.; Peng, H.-L. Biphasic alcoholysis coupled with high-speed countercurrent chromatography for high performance on separating phorbol from Croton tiglium Linn extracts. Journal of separation science 2023, 46, e2200984. doi:10.1002/jssc.202200984
  • Negi, P.; Agarwal, S.; Garg, P.; Ali, A.; Kulshrestha, S. In vivo models of understanding inflammation (in vivo methods for inflammation). Recent Developments in Anti-Inflammatory Therapy; Elsevier, 2023; pp 315–330. doi:10.1016/b978-0-323-99988-5.00017-6
  • Wender, P. A.; Gentry, Z. O.; Fanelli, D. J.; Luu-Nguyen, Q. H.; McAteer, O. D.; Njoo, E. Practical synthesis of the therapeutic leads tigilanol tiglate and its analogues. Nature chemistry 2022, 14, 1421–1426. doi:10.1038/s41557-022-01048-2
  • Damascena, H. L.; Silveira, W. A. A.; Castro, M. S.; Fontes, W. Neutrophil Activated by the Famous and Potent PMA (Phorbol Myristate Acetate). Cells 2022, 11, 2889. doi:10.3390/cells11182889
  • Chianese, G.; Amin, H. I. M.; Maioli, C.; Reddell, P.; Parsons, P.; Cullen, J.; Johns, J.; Handoko, H.; Boyle, G.; Appendino, G.; Taglialatela-Scafati, O.; Gaeta, S. Cryptic Epoxytiglianes from the Kernels of the Blushwood Tree (Fontainea picrosperma). Journal of natural products 2022, 85, 1959–1966. doi:10.1021/acs.jnatprod.2c00226
  • Zhang, T.; Liu, Z.; Sun, X.; Liu, Z.; Zhang, L.; Zhang, Q.; Peng, W.; Wu, C. Botany, traditional uses, phytochemistry, pharmacological and toxicological effects of Croton tiglium Linn.: a comprehensive review. The Journal of pharmacy and pharmacology 2022, 74, 1061–1084. doi:10.1093/jpp/rgac040
  • Williams, C. M.; Dallaston, M. A. The Future of Retrosynthesis and Synthetic Planning: Algorithmic, Humanistic or the Interplay?. Australian Journal of Chemistry 2021, 74, 291–326. doi:10.1071/ch20371
  • Chow, S.; Krainz, T.; Bettencourt, C. J.; Broit, N.; Ferguson, B.; Zhu, M.; Hull, K. G.; Pierens, G. K.; Bernhardt, P. V.; Parsons, P. G.; Romo, D.; Boyle, G. M.; Williams, C. M. Synthetic Tigliane Intermediates Engage Thiols to Induce Potent Cell Line Selective Anti-Cancer Activity. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 26, 13372–13377. doi:10.1002/chem.202003221
  • Herbrechter, R.; Beltrán, L.; Ziemba, P. M.; Titt, S.; Lashuk, K.; Gottemeyer, A.; Levermann, J.; Hoffmann, K. M.; Beltran, M.; Hatt, H.; Störtkuhl, K. F.; Werner, M.; Gisselmann, G. Effect of 158 herbal remedies on human TRPV1 and the two-pore domain potassium channels KCNK2, 3 and 9. Journal of traditional and complementary medicine 2020, 10, 446–453. doi:10.1016/j.jtcme.2020.04.005
  • Chow, S.; Krainz, T.; Bernhardt, P. V.; Williams, C. M. En Route to D-Ring Inverted Phorbol Esters. Organic letters 2019, 21, 8761–8764. doi:10.1021/acs.orglett.9b03379
  • Zimmermann, T.; Franzyk, H.; Christensen, S. B. Phorbol Rearrangements. Journal of natural products 2018, 81, 2134–2137. doi:10.1021/acs.jnatprod.8b00607
Other Beilstein-Institut Open Science Activities