Two-directional synthesis as a tool for diversity-oriented synthesis: Synthesis of alkaloid scaffolds

Kieron M. G. O’Connell, Monica Díaz-Gavilán, Warren R. J. D. Galloway and David R. Spring
Beilstein J. Org. Chem. 2012, 8, 850–860. https://doi.org/10.3762/bjoc.8.95

Supporting Information

Supporting Information File 1: Experimental procedures and spectral data for all previously unreported compounds.
Format: PDF Size: 517.3 KB Download
Supporting Information File 2: NMR Spectra of novel compounds.
Format: PDF Size: 946.9 KB Download

Cite the Following Article

Two-directional synthesis as a tool for diversity-oriented synthesis: Synthesis of alkaloid scaffolds
Kieron M. G. O’Connell, Monica Díaz-Gavilán, Warren R. J. D. Galloway and David R. Spring
Beilstein J. Org. Chem. 2012, 8, 850–860. https://doi.org/10.3762/bjoc.8.95

How to Cite

O’Connell, K. M. G.; Díaz-Gavilán, M.; Galloway, W. R. J. D.; Spring, D. R. Beilstein J. Org. Chem. 2012, 8, 850–860. doi:10.3762/bjoc.8.95

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.

Citations to This Article

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

Scholarly Works

  • Zhu, B.; Sun, T.; Chen, Z.-C.; Gao, L.; Du, W.; Chen, Y.-C. Substrate-controlled divergent synthesis withortho-vinyl-functionalised 1,3-enynes and iminesviapalladium catalysis. Organic Chemistry Frontiers 2023, 10, 3300–3306. doi:10.1039/d3qo00714f
  • Brandi, A.; Cicchi, S.; Cordero, F. M. Comprehensive Heterocyclic Chemistry IV - Bicyclic 5-6 Systems With One Bridgehead (Ring Junction) Nitrogen Atom: No Extra Heteroatom. Comprehensive Heterocyclic Chemistry IV; Elsevier, 2022; pp 437–527. doi:10.1016/b978-0-12-409547-2.14938-8
  • Kaur, N. Raney nickel-assisted nitro group reduction for the synthesis of five-membered N-heterocycles. Raney Nickel-Assisted Synthesis of Heterocycles; Elsevier, 2022; pp 1–42. doi:10.1016/b978-0-323-99492-7.00001-9
  • 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
  • Lisnyak, V. G.; Sherwood, T. C.; Snyder, S. A. The Development of Reaction Cascades to Synthesize Dimeric Coccinellid Alkaloids. Accounts of chemical research 2021, 54, 1610–1622. doi:10.1021/acs.accounts.0c00806
  • Sukhorukov, A. Y. Catalytic Reductive Amination of Aldehydes and Ketones With Nitro Compounds: New Light on an Old Reaction. Frontiers in chemistry 2020, 8, 215. doi:10.3389/fchem.2020.00215
  • Niwetmarin, W.; Campello, H. R.; Sparkes, H. A.; Aggarwal, V. K.; Gallagher, T. (-)-Cytisine: Access to a stereochemically defined and functionally flexible piperidine scaffold. Organic & biomolecular chemistry 2018, 16, 5823–5832. doi:10.1039/c8ob01456f
  • Guerola, M.; Escolano, M.; Alzuet-Piña, G.; Gómez-Bengoa, E.; de Arellano, C. R.; Sánchez-Roselló, M.; del Pozo, C. Synthesis of substituted piperidines by enantioselective desymmetrizing intramolecular aza-Michael reactions. Organic & biomolecular chemistry 2018, 16, 4650–4658. doi:10.1039/c8ob01139g
  • Yang, H.-B.; Selander, N. Divergent Iron-Catalyzed Coupling of O-Acyloximes with Silyl Enol Ethers. Chemistry (Weinheim an der Bergstrasse, Germany) 2017, 23, 1779–1783. doi:10.1002/chem.201605636
  • 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
  • Lindsay, D. M. The Synthesis of Cyclic Ether-Containing Natural and Non-natural Products by Metathesis Reactions. Topics in Heterocyclic Chemistry; Springer International Publishing, 2016; pp 33–55. doi:10.1007/7081_2015_197
  • Guerola, M.; Sánchez-Roselló, M.; Mulet, C.; del Pozo, C.; Fustero, S. Asymmetric intramolecular aza-Michael reaction in desymmetrization processes. Total synthesis of hippodamine and epi-hippodamine. Organic letters 2015, 17, 960–963. doi:10.1021/acs.orglett.5b00054
  • Procopiou, G.; Aggarwal, P.; Newton, A. F.; Richards, D.; Mellor, I. R.; Harbottle, G. W.; Stockman, R. A. Two-directional synthesis and biological evaluation of alkaloid 5-epi-cis-275B′. Chemical communications (Cambridge, England) 2014, 50, 15355–15357. doi:10.1039/c4cc07287a
  • Sherwood, T. C.; Trotta, A. H.; Snyder, S. A. A Strategy for Complex Dimer Formation When Biomimicry Fails: Total Synthesis of Ten Coccinellid Alkaloids. Journal of the American Chemical Society 2014, 136, 9743–9753. doi:10.1021/ja5045852
  • Ganguly, N. C.; Chandra, S. One-pot access to pyridocoumarins via Povarov-hydrogen transfer cascade under auto-tandem catalysis of iodine in aqueous micelles. Tetrahedron Letters 2014, 55, 1564–1568. doi:10.1016/j.tetlet.2014.01.078
  • Eschenbrenner, V.; Waldmann, H.; Kumar, K. Domino Reactions; Wiley, 2013; pp 497–521. doi:10.1002/9783527671304.ch13
  • MacLellan, P.; Nelson, A. A conceptual framework for analysing and planning synthetic approaches to diverse lead-like scaffolds. Chemical communications (Cambridge, England) 2013, 49, 2383–2393. doi:10.1039/c2cc38184b
  • Boufroura, H.; Mauduit, M.; Drège, E.; Joseph, D. Step-Economical Access to Valuable Weinreb Amide 2,5-Disubstituted Pyrrolidines by a Sequential One-Pot Two-Directional Cross-Metathesis/Cyclizing Aza-Michael Process. The Journal of organic chemistry 2013, 78, 2346–2354. doi:10.1021/jo302435a
Other Beilstein-Institut Open Science Activities