Hasubanonine

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Hasubanonine
Names
Systematic IUPAC name
3,4,7,8-Tetramethoxy-17-methyl-7,8-didehydrohasubanan-6-one
Other names
Hasubanonine
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C21H27NO5/c1-22-11-10-20-12-14(23)17(25-3)19(27-5)21(20,22)9-8-13-6-7-15(24-2)18(26-4)16(13)20/h6-7H,8-12H2,1-5H3/t20-,21+/m0/s1 checkY
    Key: DXUSNRCTWFHYFS-LEWJYISDSA-N checkY
  • InChI=1/C21H27NO5/c1-22-11-10-20-12-14(23)17(25-3)19(27-5)21(20,22)9-8-13-6-7-15(24-2)18(26-4)16(13)20/h6-7H,8-12H2,1-5H3/t20-,21+/m0/s1
    Key: DXUSNRCTWFHYFS-LEWJYISDBB
  • O=C4C(\OC)=C(\OC)[C@]23N(CC[C@@]3(c1c(ccc(OC)c1OC)CC2)C4)C
Properties
C21H27NO5
Molar mass 373.449 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Hasubanonine is a member of the hasubanan family of alkaloids. The alkaloid with an isoquinoline substructure has the molecular formula of C21H27NO5.[1] The enantiomer of the natural product is being studied as a potential painkiller.[2] Hasubanonine is structurally related to the morphinan class of opioid analgesics.

The enantioselective total synthesis of (–)-hasubanonine and related natural products, (−)-runanine, (−)-delavayine, and (+)-periglaucine B were first achieved by Prof. Seth Herzon and co-workers at Yale University in 2011. [3]

References

  1. ^ Hasubanonine
  2. ^ "Y. Chemists hoping to ease pain". Deseret News. August 17, 2006.
  3. ^ Herzon, Seth B.; Calandra, Nicholas A.; King, Sandra M.; McCarthy, M. C.; Gauss, J. (2011). "Efficient Entry to the Hasubanan Alkaloids: First Enantioselective Total Syntheses of (−)-Hasubanonine, (−)-Runanine, (−)-Delavayine, and (+)-Periglaucine B". Angewandte Chemie International Edition. 50 (38): 8863–8866. doi:10.1002/anie.201102226. PMID 21638524.


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