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Structure of the Lycorinine Alkaloid Nobilisitine A

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Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra ACT 0200, Australia
E-mail: [email protected]
Cite this: J. Org. Chem. 2011, 76, 20, 8560–8563
Publication Date (Web):September 7, 2011
https://doi.org/10.1021/jo2016899
Copyright © 2011 American Chemical Society
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Abstract

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The structure 3 recently proposed, on the basis of computed NMR chemical shifts, for the natural product nobilisitine A has been synthesized from its C5-epimer (+)-clividine (4). The spectral data derived from compound 3 match those reported for the natural product.

Supporting Information

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CIF files, crystallographic data, and anisotropic displacement ellipsoid plots derived from the single-crystal X-ray analyses of compounds 3 and 6; Tables S1–S3 comparing spectral data derived from compound ent-1, nobilistine A, and compound 3; 1H and 13C NMR spectra for compounds 3 and 5–7. This material is available free of charge via the Internet at http://pubs.acs.org.

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Cited By

This article is cited by 20 publications.

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  2. Isabel S. Hernandes, Haroldo C. Da Silva, Hélio F. Dos Santos, Wagner B. De Almeida. Conformational Analysis of 5,4′-Dihydroxy-7,5′,3′-trimethoxyisoflavone in Solution Using 1H NMR: A Density Functional Theory Approach. The Journal of Physical Chemistry A 2020, 124 (25) , 5182-5193. https://doi.org/10.1021/acs.jpca.0c02996
  3. Ping Lan, Lauren E. White, Ehab S. Taher, Prudence E. Guest, Martin G. Banwell, and Anthony C. Willis . Chemoenzymatic Synthesis of (+)-Asperpentyn and the Enantiomer of the Structure Assigned to Aspergillusol A. Journal of Natural Products 2015, 78 (8) , 1963-1968. https://doi.org/10.1021/acs.jnatprod.5b00304
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  7. Strahil Berkov, Edison Osorio, Francesc Viladomat, Jaume Bastida. Chemodiversity, chemotaxonomy and chemoecology of Amaryllidaceae alkaloids. 2020,,, 113-185. https://doi.org/10.1016/bs.alkal.2019.10.002
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  14. Derek R. Boyd, Narain D. Sharma, Magdalena Kaik, Peter B. A. McIntyre, John F. Malone, Paul J. Stevenson. Reactions of enantiopure cyclic diols with sulfuryl chloride. Org. Biomol. Chem. 2014, 12 (13) , 2128-2136. https://doi.org/10.1039/C4OB00042K
  15. Martin G. Banwell, Matthew T. Jones, Tristan A. Reekie, Brett D. Schwartz, Shen H. Tan, Lorenzo V. White. RANEY® cobalt – an underutilised reagent for the selective cleavage of C–X and N–O bonds. Org. Biomol. Chem. 2014, 12 (38) , 7433-7444. https://doi.org/10.1039/C4OB00917G
  16. Derek R. Boyd, Narain D. Sharma, Tayeb Belhocine, John F. Malone, Stuart T. McGregor, Jordan Atchison, Peter A. B. McIntyre, Paul J. Stevenson. Reactions of nitrogen nucleophiles with enantiopure cyclohexenyl electrophiles: a stereo- and regio- selective study. Journal of Physical Organic Chemistry 2013, 26 (12) , 997-1008. https://doi.org/10.1002/poc.3183
  17. Zhong Jin. Amaryllidaceae and Sceletium alkaloids. Natural Product Reports 2013, 30 (6) , 849. https://doi.org/10.1039/c3np70005d
  18. Dean J. Tantillo. Walking in the woods with quantum chemistry – applications of quantum chemical calculations in natural products research. Natural Product Reports 2013, 30 (8) , 1079. https://doi.org/10.1039/c3np70028c
  19. Miriam Corredor, Jordi Bujons, Àngel Messeguer, Ignacio Alfonso. 15N NMR spectroscopic and theoretical GIAO-DFT studies for the unambiguous characterization of disubstituted 1,2,3-triazoles. Organic & Biomolecular Chemistry 2013, 11 (42) , 7318. https://doi.org/10.1039/c3ob41587b
  20. Steven M. Bachrach. Computational organic chemistry. Annual Reports Section "B" (Organic Chemistry) 2012, 108 , 334. https://doi.org/10.1039/c2oc90002e

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