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Lythranidine

Lythranidine
Names
Systematic IUPAC name
(9S,11R,15R,17S)-23-Methoxy-25-azatetracyclo[18.3.1.12,6.111,15]hexacosa-1(24),2,4,6(26),20,22-hexaene-3,9,17-triol
Identifiers
3D model (JSmol)
1555440
ChEBI
ChemSpider
  • InChI=1S/C26H35NO4/c1-31-26-12-8-18-6-10-22(29)16-20-4-2-3-19(27-20)15-

    21(28)9-5-17-7-11-25(30)23(13-17)24(26)14-18/h7-8,11-14,19-22,27-30H,

    2-6,9-10,15-16H2,1H3
  • COC1=C2C=C(CCC(CC3CCCC(N3)CC(CCC4=CC2=C(C=C4)O)O)O)C=C1
Properties
C26H35NO4
Molar mass 425.569 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lythranidine is a piperidine alkaloid that was first isolated from the plant Lythrum anceps.[1] It contains a 17-membered cyclophane ring.

Several laboratory syntheses have been reported.[2][3][4][5]

References

  1. ^ Fujita, E; Fuji, K (1971). "Lythraceous alkaloids. Part IV. Structure and absolute configuration of lythranine, lythranidine, and lythramine". Journal of the Chemical Society C: Organic: 1651. doi:10.1039/J39710001651.
  2. ^ Fuji, Kaoru; Ichikawa, Kohei; Fujita, Eiichi (1980). "Lythraceous alkaloids. Part 11. Total synthesis of (±)-lythranidine". J. Chem. Soc., Perkin Trans. 1: 1066–1069. doi:10.1039/P19800001066.
  3. ^ Carruthers, William; Coggins, Peter; Weston, John B (1991). "Nitrone cycloaddition: An approach to the cyclophane alkaloid (±)-lythranidine". J. Chem. Soc., Perkin Trans. 1 (3): 611–616. doi:10.1039/P19910000611.
  4. ^ Pinder, A. R (1992). "Azetidine, pyrrole, pyrrolidine, piperidine, and pyridine alkaloids". Natural Product Reports. 9 (5): 491. doi:10.1039/NP9920900491.
  5. ^ Gebauer, Konrad; Fürstner, Alois (2014). "Total Synthesis of the Biphenyl Alkaloid (−)-Lythranidine" (PDF). Angewandte Chemie International Edition. 53 (25): 6393–6396. doi:10.1002/anie.201402550. PMID 24821137.


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