Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 51, 2021 - Issue 2
368
Views
2
CrossRef citations to date
0
Altmetric
Articles

Synthesis of the ester side chains of homoharringtonine and harringtonine using lactones as building blocks

, , &
Pages 317-323 | Received 24 Apr 2020, Published online: 12 Oct 2020

References

  • For reviews, see: (a) Huang, L.; Xue, Z. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; Academic Press: New York, 1984; Vol. 23, pp 157–226. (b) Hudlicky, T.; Kwart, L. D.; Reed, J. W.; In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W. Ed.; John Wiley and Sons: New York, 1987; Vol. 5, pp 639–690. (c) Jalil Miah, M. A.; Hudlicky, T.; Reed, J. W. In The Alkaloids; Brossi, A.; Ed.; Academic Press: New York, 1998; Vol. 51, pp 199–269. (d) Hudlicky, T.; Reed, J. W. The Way of Synthesis: Evolution of Design and Methods for Natural Products; Wiley-VCH: Weinheim, Germany, 2007; Part 4.5, pp 655–687. (e) Abdelkafi, H.; Nay, B. Nat. Prod. Rep. 2012, 29, 845–869. DOI: 10.1039/c2np20037f. (f) Chen, Y.; Li, W.-D. Z. Chin. J. Org. Chem (Youji Huaxue). 2017, 37, 1885. Accession Number 2017:1570351. (g) Pérard-Viret, J.; Quteishat, L.; Alsalim, R.; Royer, J.; Dumas, F. In The Alkaloids: Chemistry and Biology; Knölker, H.-J., Ed.; Elsevier: Amsterdam, 2017, Vol. 78, pp 205–352.
  • (a) Wetzler, M.; Segal, D. Curr. Pharm. Des. 2011, 17, 59–64. DOI: 10.2174/138161211795049778. (b) Kantarjian, H. M.; O'Brien, S.; Cortes, J. Clin. Lymphoma Myeloma Leuk 2013, 13, 530–533. DOI: 10.1016/j.clml.2013.03.017.
  • For recent reports, see: (a) Xing, P.; Huang, Z.-G.; Jin, Y.; Jiang, B, Synthesis 2013, 45, 596–600. DOI: 10.1055/s-0032-1318116. (b) Xiao, K.-J.; Luo, J.-M.; Xia, X.-E.; Wang, Y.; Huang, P.-Q. Chem. Eur. J. 2013, 19, 13075–13086. DOI: 10.1002/chem.201302096. (c) Liu, H.; Yu, J.; Li, X.; Yan, R.; Xiao, J.-C.; Hong, R. Org. Lett. 2015, 17, 4444–4447. DOI: 10.1021/acs.orglett.5b02106. (d) Huang, S.-H.; Tian, X.; Mi, X.; Wang, Y.; Hong, R. Tetrahedron Lett. 2015, 56, 6656–6658. DOI: 10.1016/j.tetlet.2015.10.002. (e) Marguerit, M.; Little, G.; Wang, Y.; He, L.; Allwein, S.; Reif, J.; Rossi, J.; Roemmele, R.; Bakale, R. Eur. J. Org. Chem. 2015, 2015, 8003–8010. DOI: 10.1002/ejoc.201500906. (f) Couthami, P.; Chegondi, R.; Chandrasekhar, S. Org. Lett. 2016, 18, 2044. (g) Ma, X.-Y.; An, X.-T.; Zhao, X.-H.; Du, J.-Y.; Deng, Y.-H.; Zhang, X.-Z.; Fan, C.-A. Org. Lett. 2017, 19, 2965–2968. DOI: 10.1021/acs.orglett.7b01202. (h) Siitonen, J. H.; Yu, L.; Danielsson, J.; Gregorio, G. D.; Somfai, P. J. Org. Chem. 2018, 83, 11318–11322. DOI: 10.1021/acs.joc.8b01540. (i) Ju, X.; Beaudry, C. M. Angew. Chem. Int. Ed. Engl. 2019, 58, 6752–6755.
  • Hiranuma, S.; Shibata, M.; Hudlicky, T. J. Org. Chem. 1983, 48, 5321–5326. DOI: 10.1021/jo00174a031.
  • (a) Zhao, Z.-Z.; Xi, Y.-G.; Zhao, H.-F.; Hou, J.-Y.; Zhang, J.-Y.; Wang, Z.-H. Acta Pharmaceutica Sinica 1980, 15, 46; Chem. Abstr. 1980, 94, 103627. (b) Wang, Y.-K.; Li, Y.-L.; Pan, X.-F.; Li, S.-B.; Huang, W.-K. Chin. Sci. Bull. 1980, 25, 576. (c) Hiranuma, S.; Hudlicky, T. Tetrahedron Lett. 1982, 23, 3431–3434. DOI: 10.1016/S0040-4039(00)87634-0. (d) Cheng, J.-C.; Zhang, J.-H.; Zhang, Q.-B.; Yang, J.; Huang, L. Acta Pharm. Sinica 1984, 19, 178; Chem. Abstr. 1984, 103, 160738. (e) Wang, Y.; Li, Y.; Pan, X.; Li, S.; Huang, W. Acta Chim. Sinica 1985, 43, 161.
  • Ma, G.-Z.; Li, P.-F.; Liu, L.; Li, W.-D. Z.; Chen, L. Org. Lett. 2017, 19, 2250–2253. DOI: 10.1021/acs.orglett.7b00743.
  • Robin, J.-P.; Dhal, R.; Dujardin, G.; Girodier, L.; Mevellec, L.; Poutot, S. Tetrahedron Lett. 1999, 40, 2931–2934. DOI: 10.1016/S0040-4039(99)00327-5.
  • Ancliff, R. A.; Russell, A. T.; Sanderson, A. J. Chem. Commun. 2006, 2006, 3243. DOI: 10.1039/b605339d.
  • (a) Eckelbarger, J. D.; Wilmot, J. T.; Gin, D. Y. J. Am. Chem. Soc. 2006, 128, 10370–10371. DOI: 10.1021/ja063304f. (b) Eckelbarger, J. D.; Wilmot, J. T.; Epperson, M. T.; Thakur, C. S.; Shum, D.; Antczak, C.; Tarassishin, L.; Djaballah, H.; Gin, D. Y. Chemistry 2008, 14, 4293–4306. DOI: 10.1002/chem.200701998.
  • (a) Zhang, Z.-W.; Zhang, X.-F.; Feng, J.; Yang, Y.-H.; Wang, C.-C.; Feng, J.-C.; Liu, S. J. Org. Chem. 2013, 78, 786–790. DOI: 10.1021/jo302608a. (b) Lian, W.-F.; Wang, C.-C.; Kang, H.-P.; Li, H.-L.; Feng, J.; Liu, S.; Zhang, Z.-W. Tetrahedron Lett. 2017, 58, 1399–1402. DOI: 10.1016/j.tetlet.2017.02.064. (c) Zhang, Z.-W.; Wang, C.-C.; Xue, H.; Dong, Y.; Yang, J.-H.; Liu, S.; Liu, W.-Q.; Li, W.-D. Z. Org. Lett. 2018, 20, 1050–1053. DOI: 10.1021/acs.orglett.7b04008. (d) Dong, Y.; Li, H.; Li, J.; Feng, L.; Zhang, Z.-W. Prog. Chem. 2018, 30, 1827.
  • Geibel, I.; Dierks, A.; Müller, T.; Christoffers, J. Chemistry 2017, 23, 7245–7254. DOI: 10.1002/chem.201605468.
  • Kanemitsu, T.; Sato, M.; Yoshida, M.; Ozasa, E.; Miyazaki, M.; Odanaka, Y.; Nagata, K.; Itoh, T. Org. Lett. 2016, 18, 5484–5487. DOI: 10.1021/acs.orglett.6b02682.
  • (a) Keller, L.; Dumas, F.; d'Angelo, J. Tetrahedron Lett. 2001, 42, 1911–1913. DOI: 10.1016/S0040-4039(01)00086-7. (b) Keller, L.; Dumas, F.; d’Angelo, J. Eur. J. Org. Chem. 2003, 2003, 2488–2497. DOI: 10.1002/ejoc.200300111.
  • El Bialy, S. A. A.; Braun, H.; Tietze, L. F. Eur. J. Org. Chem. 2005, 2005, 2965–2972. DOI: 10.1002/ejoc.200500065.
  • (a) Yang, H.; Sun, M.; Zhao, S.; Zhu, M.; Xie, Y.; Niu, C.; Li, C. J. Org. Chem. 2013, 78, 339–346. DOI: 10.1021/jo302203g. (b) Sun, M. R.; Zhou, H.; Cao, Q.-W.; Gao, K.-G.; Yang, H. Huaxue Yanjiu 2013, 4, 416; Chem. Abstr. 2014, 166, 517527. (c) Sun, M.; Jia, X.; Lai, Y.; Yang, H. J. Chem. Res. 2015, 39, 26–29. DOI: 10.3184/174751915X14189228913336.
  • Berhal, F.; Tardy, S.; Pérard-Viret, J.; Royer, J. Eur. J. Org. Chem. 2009, 2009, 437–443. DOI: 10.1002/ejoc.200800935.
  • Craig, R. A.; II, Loskot, S. A.; Mohr, J. T.; Behenna, D. C.; Harned, A. M.; Stoltz, B. M. Org. Lett. 2015, 17, 5160–5163. DOI: 10.1021/acs.orglett.5b02376.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.