Chemistry:Hasubanonine
From HandWiki
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| Names | |
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| Systematic IUPAC name
3,4,7,8-Tetramethoxy-17-methyl-7,8-didehydrohasubanan-6-one | |
| Other names
Hasubanonine
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| UNII | |
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| 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). | |
 verify (what is   ?)
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| Infobox references | |
Tracking categories (test):
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
- ↑ Hasubanonine
- ↑ "Y. Chemists hoping to ease pain". Deseret News. August 17, 2006. http://deseretnews.com/dn/view/0,1249,645193786,00.html.
- ↑ 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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