Plakoridine A

Plakoridine A is an alkaloid isolated from the marine sponge Plakortis sp.[1][2] There are three plakoridines known, named plakoridine A, B, and C.[3][4]

Plakoridine A
Names
Systematic IUPAC name
Methyl (2S,3S,4R,5E)-4-hydroxy-1-[2-(4-hydroxyphenyl)ethyl]-5-(2-oxooctadecylidene)-2-propyl-3-pyrrolidinecarboxylate
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C35H57NO5/c1-4-6-7-8-9-10-11-12-13-14-15-16-17-18-20-30(38)27-32-34(39)33(35(40)41-3)31(19-5-2)36(32)26-25-28-21-23-29(37)24-22-28/h21-24,27,31,33-34,37,39H,4-20,25-26H2,1-3H3/b32-27+/t31-,33-,34-/m0/s1
    Key: ULFKEEJTLUNSEY-CWJJWNJISA-N
  • O=C(/C=C2/N(CCc1ccc(O)cc1)[C@H]([C@H](C(=O)OC)[C@H]2O)CCC)CCCCCCCCCCCCCCCC
Properties
C35H57NO5
Molar mass 571.843 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Takeuchi, Shinji; Ishibashi, Masami; Kobayashi, Junichi (1994). "Plakoridine A, a new tyramine-containing pyrrolidine alkaloid from the Okinawan marine sponge Plakortis sp". The Journal of Organic Chemistry. 59 (13): 3712–3713. doi:10.1021/jo00092a039.
  2. Ma, Dawei; Sun, Haiying (2000). "Total synthesis of (2S,3S,4R)-plakoridine A". Tetrahedron Letters. 41 (12): 1947–1950. doi:10.1016/S0040-4039(00)00096-4.
  3. Ishiguro, Yuichiro; Kubota, Takaaki; Ishiuchi, Kan’ichiro; Fromont, Jane; Kobayashi, Jun’ichi (July 2009). "Plakoridine C, a novel piperidine alkaloid from an Okinawan marine sponge Plakortis sp". Tetrahedron Letters. 50 (26): 3202–3204. doi:10.1016/j.tetlet.2009.01.135.
  4. Norris, Matthew D.; Perkins, Michael V. (2016). "Structural diversity and chemical synthesis of peroxide and peroxide-derived polyketide metabolites from marine sponges". Natural Product Reports. 33 (7): 861–880. doi:10.1039/C5NP00142K.


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