Analogues of amphibian alkaloids: total synthesis of (5R,8S,8aS)-(−)-8-methyl-5-pentyloctahydroindolizine (8-epi-indolizidine 209B) and [(1S,4R,9aS)-(−)-4-pentyloctahydro-2H-quinolizin-1-yl]methanol

Joseph P. Michael, Claudia Accone, Charles B. de Koning and Christiaan W. van der Westhuyzen
Beilstein J. Org. Chem. 2008, 4, No. 5. https://doi.org/10.1186/1860-5397-4-5

Supporting Information

Supporting Information File 1: Analogues of amphibian alkaloids - Full experimental details. The Supporting Information File contains detailed experimental procedures and full characterisation data for all new compounds prepared during the synthesis of the two title compounds.
Format: DOC Size: 120.5 KB Download

Cite the Following Article

Analogues of amphibian alkaloids: total synthesis of (5R,8S,8aS)-(−)-8-methyl-5-pentyloctahydroindolizine (8-epi-indolizidine 209B) and [(1S,4R,9aS)-(−)-4-pentyloctahydro-2H-quinolizin-1-yl]methanol
Joseph P. Michael, Claudia Accone, Charles B. de Koning and Christiaan W. van der Westhuyzen
Beilstein J. Org. Chem. 2008, 4, No. 5. https://doi.org/10.1186/1860-5397-4-5

How to Cite

Michael, J. P.; Accone, C.; de Koning, C. B.; van der Westhuyzen, C. W. Beilstein J. Org. Chem. 2008, 4, No. 5. doi:10.1186/1860-5397-4-5

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

  • Kaur, N. Six-membered N-heterocycles: Alkenes. Iodine-Assisted Synthesis of Six- and Seven-Membered Heterocycles; Elsevier, 2023; pp 1–29. doi:10.1016/b978-0-443-15225-2.00017-7
  • Kaur, N. Five-Membered S-Heterocycle Synthesis. Lawesson's Reagent in Heterocycle Synthesis; Springer Singapore, 2021; pp 149–174. doi:10.1007/978-981-16-4655-3_5
  • Kaur, N. Five-Membered N-Heterocycle Synthesis. Lawesson's Reagent in Heterocycle Synthesis; Springer Singapore, 2021; pp 1–33. doi:10.1007/978-981-16-4655-3_1
  • Mohajer, F.; Ziarani, G. M.; Moradi, R. The Study of Several Synthesis Methods of Indolizidine (±)-209I and (±)-209B as Natural Alkaloids. Current Organic Chemistry 2020, 24, 516–535. doi:10.2174/1385272824666200226113022
  • Klintworth, R.; de Koning, C. B.; Opatz, T.; Michael, J. P. A Xylochemically Inspired Synthesis of Lamellarin G Trimethyl Ether via an Enaminone Intermediate. The Journal of organic chemistry 2019, 84, 11025–11031. doi:10.1021/acs.joc.9b01604
  • Morgans, G. L.; Fernandes, M. A.; van Otterlo, W. A. L.; Michael, J. P. Base‐Mediated Cyclization of 3‐[2‐(2‐Oxo‐2‐phenylethyl)‐1‐pyrrolidinyl]propanenitrile to 7‐Phenyl‐1,2,3,7,8,8a‐hexahydroindolizine‐6‐carbonitrile: What Lies Between?. European Journal of Organic Chemistry 2018, 2018, 1902–1909. doi:10.1002/ejoc.201701714
  • Riley, D. L.; Michael, J. P.; de Koning, C. B. New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates. Beilstein journal of organic chemistry 2016, 12, 2609–2613. doi:10.3762/bjoc.12.256
  • Wong, H.; Garnier-Amblard, E. C.; Liebeskind, L. S. Organometallic enantiomeric scaffolding: a strategy for the enantiocontrolled construction of regio- and stereodivergent trisubstituted piperidines from a common precursor. Journal of the American Chemical Society 2011, 133, 7517–7527. doi:10.1021/ja201012p
  • Sridharan, V.; Maiti, S.; Menéndez, J. C. A Very Efficient Cerium(IV) Ammonium Nitrate Catalyzed, Four‐Component Synthesis of Tetrahydropyridines and Its Application in the Concise Generation of Functionalized Homoquinolizine Frameworks. Chemistry (Weinheim an der Bergstrasse, Germany) 2009, 15, 4565–4572. doi:10.1002/chem.200900044
  • Neto, B. A. D.; Lapis, A. A. M.; Bernd, A. B.; Russowsky, D. Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids. Tetrahedron 2009, 65, 2484–2496. doi:10.1016/j.tet.2009.01.081
  • de Koning, C. B.; Michael, J. P.; Riley, D. L. Formal synthesis of (5R,8R,8aS)-indolizidine 209I via enaminones incorporating Weinreb amides. HETEROCYCLES 2009, 79, 935–953. doi:10.3987/com-08-s(d)68
Other Beilstein-Institut Open Science Activities