Total synthesis of (−)-epimyrtine by a gold-catalyzed hydroamination approach

Scholarly Works

• Gantasala, N.; Fournet, C.; Le Roch, M.; Lalli, C.; Pabbaraja, S.; Gouault, N. Accessing spiropiperidines from dihydropyridones through tandem triflation-allylation and ring-closing metathesis (RCM). Organic & biomolecular chemistry 2023, 21, 5245–5253. doi:10.1039/d3ob00545c
• Bardasov, I. N.; Ievlev, M. Y. Comprehensive Heterocyclic Chemistry IV - Bicyclic 6-6 Systems With One Bridgehead (Ring Junction) Nitrogen Atom: No Extra Heteroatom. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 1–61. doi:10.1016/b978-0-12-409547-2.14916-9
• Praveen, C. Cycloisomerization of π-Coupled Heteroatom Nucleophiles by Gold Catalysis: En Route to Regiochemically Defined Heterocycles. Chemical record (New York, N.Y.) 2021, 21, 1697–1737. doi:10.1002/tcr.202100105
• Worch, J. C.; Stubbs, C. J.; Price, M. J.; Dove, A. P. Click Nucleophilic Conjugate Additions to Activated Alkynes: Exploring Thiol-yne, Amino-yne, and Hydroxyl-yne Reactions from (Bio)Organic to Polymer Chemistry. Chemical reviews 2021, 121, 6744–6776. doi:10.1021/acs.chemrev.0c01076
• Campeau, D.; Rayo, D. F. L.; Mansour, A.; Muratov, K.; Gagosz, F. Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes. Chemical reviews 2020, 121, 8756–8867. doi:10.1021/acs.chemrev.0c00788
• Phillips, A. M. F.; Martins, L. M. D. R. S.; Pombeiro, A. J. L. Synthetic Approaches to Nonaromatic Nitrogen Heterocycles; Wiley, 2020; pp 119–160. doi:10.1002/9781119708841.ch6
• Stojanović, M.; Bugarski, S.; Baranac-Stojanović, M. Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones. The Journal of organic chemistry 2020, 85, 13495–13507. doi:10.1021/acs.joc.0c01537
• Bates, R. W.; Ko, W.; Barát, V. The endo-aza-Michael addition in the synthesis of piperidines and pyrrolidines. Organic & biomolecular chemistry 2020, 18, 810–829. doi:10.1039/c9ob02388g
• Wang, Z. Advances in the Asymmetric Total Synthesis of Natural Products Using Chiral Secondary Amine Catalyzed Reactions of α,β-Unsaturated Aldehydes. Molecules (Basel, Switzerland) 2019, 24, 3412. doi:10.3390/molecules24183412
• Lahosa, A.; Yus, M.; Foubelo, F. Enantiodivergent Approach to the Synthesis of Cis-2,6-Disubstituted Piperidin-4-ones. The Journal of organic chemistry 2019, 84, 7331–7341. doi:10.1021/acs.joc.9b01008
• Yongsheng, C.; Liu, S.; Cui, P.; Zhang, Y.; Liu, Q.; Zhou, H. Metal-free one-pot three-step process for the direct conversion of aryl alkynes into secondary amines with TfOH/B2(OH)4. Tetrahedron Letters 2019, 60, 327–330. doi:10.1016/j.tetlet.2018.12.041
• Obydennov, D. L.; El-Tantawy, A. I.; Sosnovskikh, V. Y. Synthesis of Multifunctionalized 2,3-Dihydro-4-pyridones and 4-Pyridones via the Reaction of Carbamoylated Enaminones with Aldehydes. The Journal of organic chemistry 2018, 83, 13776–13786. doi:10.1021/acs.joc.8b02075
• Pflästerer, D.; Rudolph, M.; Hashmi, A. S. K. Gold-Catalyzed Hydrofunctionalizations and Spiroketalizations of Alkynes as Key Steps in Total Synthesis. Israel Journal of Chemistry 2018, 58, 622–638. doi:10.1002/ijch.201700056
• Kandepedu, N.; Abrunhosa-Thomas, I.; Troin, Y. Stereoselective strategies for the construction of polysubstituted piperidinic compounds and their applications in natural products’ synthesis. Organic Chemistry Frontiers 2017, 4, 1655–1704. doi:10.1039/c7qo00262a
• Benimana, S. E.; Cromwell, N. E.; Meer, H. N.; Marvin, C. C. Visible light photoredox and Polonovski-Potier cyclizations for the synthesis of (±)-5-epi-cermizine C and (±)-epimyrtine. Tetrahedron Letters 2016, 57, 5062–5064. doi:10.1016/j.tetlet.2016.10.007
• Esmaeili-Marandi, F.; Yavari, I.; Saeedi, M.; Mahdavi, M.; Shafiee, A. Synthesis of Novel Pyrazino[2,1‐a]isoindolediones via Intramolecular Hydroamination of 2,3‐Dihydro‐3‐oxo‐2‐(prop‐2‐yn‐1‐yl)‐1H‐isoindole‐1‐carboxamides. Helvetica Chimica Acta 2016, 99, 187–190. doi:10.1002/hlca.201500168
• Pflästerer, D.; Hashmi, A. S. K. Gold catalysis in total synthesis – recent achievements. Chemical Society reviews 2016, 45, 1331–1367. doi:10.1039/c5cs00721f
• Wang, Y.-H.; Cao, Z.-Y.; Zhou, J. Gold Catalysis in the Synthesis of Natural Products: Heterocycle Construction via Direct C–X-Bond-Forming Reactions. Topics in Heterocyclic Chemistry; Springer International Publishing, 2016; pp 249–283. doi:10.1007/7081_2015_5007
• Debrouwer, W.; Heugebaert, T. S. A.; Roman, B.; Stevens, C. V. Homogeneous Gold-Catalyzed Cyclization Reactions of Alkynes with N- and S-Nucleophiles. Advanced Synthesis & Catalysis 2015, 357, 2975–3006. doi:10.1002/adsc.201500520
• Guieu, B.; Le Roch, M.; David, M.; Gouault, N. Gold-catalyzed synthesis of enantioenriched furfurylamines from amino acids. Tetrahedron: Asymmetry 2015, 26, 868–875. doi:10.1016/j.tetasy.2015.06.014

Explore citations to this article at