Flexible synthesis of poison-frog alkaloids of the 5,8-disubstituted indolizidine-class. II: Synthesis of (-)-209B, (-)-231C, (-)-233D, (-)-235B", (-)-221I, and an epimer of 193E and pharmacological effects at neuronal nicotinic acetylcholine receptors

Soushi Kobayashi, Naoki Toyooka, Dejun Zhou, Hiroshi Tsuneki, Tsutomu Wada, Toshiyasu Sasaoka, Hideki Sakai, Hideo Nemoto, H. Martin Garraffo, Thomas F. Spande and John W. Daly
Beilstein J. Org. Chem. 2007, 3, No. 30. https://doi.org/10.1186/1860-5397-3-30

Supporting Information

Supporting Information File 1: Experimental details for the synthesis of (-)-209B, (-)-231C, (-)-233D, (-)-235B", (-)-221I, and an epimer of 193E and pharmacological effects at neuronal nicotinic acetylcholine receptors. Experimental data which includes experimental details on the spectral instruments, elemental analyzer.
Format: DOC Size: 86.0 KB Download

Cite the Following Article

Flexible synthesis of poison-frog alkaloids of the 5,8-disubstituted indolizidine-class. II: Synthesis of (-)-209B, (-)-231C, (-)-233D, (-)-235B", (-)-221I, and an epimer of 193E and pharmacological effects at neuronal nicotinic acetylcholine receptors
Soushi Kobayashi, Naoki Toyooka, Dejun Zhou, Hiroshi Tsuneki, Tsutomu Wada, Toshiyasu Sasaoka, Hideki Sakai, Hideo Nemoto, H. Martin Garraffo, Thomas F. Spande and John W. Daly
Beilstein J. Org. Chem. 2007, 3, No. 30. https://doi.org/10.1186/1860-5397-3-30

How to Cite

Kobayashi, S.; Toyooka, N.; Zhou, D.; Tsuneki, H.; Wada, T.; Sasaoka, T.; Sakai, H.; Nemoto, H.; Garraffo, H. M.; Spande, T. F.; Daly, J. W. Beilstein J. Org. Chem. 2007, 3, No. 30. doi:10.1186/1860-5397-3-30

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

  • Nay, B. Total synthesis: an enabling science. Beilstein journal of organic chemistry 2023, 19, 474–476. doi:10.3762/bjoc.19.36
  • 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
  • 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
  • Beng, T. K.; Langevin, S.; Farah, A. O.; Goodsell, J.; Wyatt, K. One-shot access to isoquinolone and (hetero)izidinone architectures using cyclic α-chloro eneformamides and cyclic anhydrides. New Journal of Chemistry 2019, 43, 5282–5286. doi:10.1039/c8nj06539j
  • Toyooka, N.; Takashima, K. Formal Synthesis of Gephyrotoxin 287C. HETEROCYCLES 2019, 99, 649. doi:10.3987/com-18-s(f)25
  • Rodriguez, C.; Rollins-Smith, L. A.; Ibáñez, R.; Durant-Archibold, A. A.; Gutiérrez, M. Toxins and pharmacologically active compounds from species of the family Bufonidae (Amphibia, Anura). Journal of ethnopharmacology 2016, 198, 235–254. doi:10.1016/j.jep.2016.12.021
  • Rao, H. S. P.; Rao, A. V. B.; Shanmugam, S. Copper(II) Bromide–Catalyzed C-C/C-N Bond-Forming Reactions: Synthesis of Pyrrole-Incorporated Triarylmethanes. Synthetic Communications 2015, 45, 2712–2717. doi:10.1080/00397911.2015.1100746
  • Budzikiewicz, H. Mass Spectrometry in Natural Product Structure Elucidation. Progress in the chemistry of organic natural products 2014, 100, 77–221. doi:10.1007/978-3-319-05275-5_2
  • Abels, F.; Lindemann, C.; Schneider, C. A General Strategy for the Catalytic, Highly Enantio- and Diastereoselective Synthesis of Indolizidine-Based Alkaloids. Chemistry (Weinheim an der Bergstrasse, Germany) 2014, 20, 1964–1979. doi:10.1002/chem.201304086
  • Wang, X.; Tsuneki, H.; Urata, N.; Tezuka, Y.; Wada, T.; Sasaoka, T.; Sakai, H.; Saporito, R. A.; Toyooka, N. Synthesis and Biological Activities of the 3,5‐Disubstituted Indolizidine Poison Frog Alkaloid 239Q and Its Congeners. European Journal of Organic Chemistry 2012, 2012, 7082–7092. doi:10.1002/ejoc.201200974
  • 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
  • Toyooka, N.; Zhou, D.; Nemoto, H.; Tezuka, Y.; Kadota, S.; Andriamaharavo, N. R.; Garraffo, H. M.; Spande, T. F.; Daly, J. W. Efficient enantio- and diastereodivergent synthesis of poison-frog alkaloids 251O and trans-223B. The Journal of organic chemistry 2009, 74, 6784–6791. doi:10.1021/jo901100m
  • Zhou, D.; Toyooka, N.; Nemoto, H.; Yamaguchi, K.; Tsuneki, H.; Wada, T.; Sasaoka, T.; Sakai, H.; Tezuka, Y.; Kadota, S.; Jones, T. H.; Garraffo, H. M.; Spande, T. F.; Daly, J. W. Synthesis, Determination of the Absolute Stereochemistry, and Evaluations at the Nicotinic Acetylcholine Receptors of a Hydroxyindolizidine Alkaloid from the Ant Myrmicaria melanogaster. HETEROCYCLES 2009, 79, 565–571. doi:10.3987/com-08-s(d)16
  • 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
  • Nelson, A.; Garraffo, H. M.; Spande, T. F.; Daly, J. W.; Stevenson, P. J. Facile synthesis of two diastereomeric indolizidines corresponding to the postulated structure of alkaloid 5,9E-259B from a Bufonid toad (Melanophryniscus). Beilstein journal of organic chemistry 2008, 4, 6. doi:10.1186/1860-5397-4-6
Other Beilstein-Institut Open Science Activities