Erysodienone
Chemical compound
From Wikipedia, the free encyclopedia
Erysodienone is a key precursor in the biosynthesis of many Erythrina-produced alkaloids.[1] Early work was done by Derek Barton and co-workers to illustrate the biosynthetic pathways towards erythrina alkaloids.[2][3][4] It was demonstrated that erysodienone could be synthesized from simple starting materials by a similar approach as its biosynthetic pathway, which led to the development of the biomimetic synthesis of erysodienone.[5]
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| Names | |
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| IUPAC name
16-Hydroxy-3,15-dimethoxy-1,3,4,6-tetradehydroerythrinan-2-one | |
| Systematic IUPAC name
(9bS)-7-Hydroxy-8,11-dimethoxy-1,2,4,5-tetrahydro-12H-indolo[7a,1-a]isoquinolin-12-one | |
| Identifiers | |
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CompTox Dashboard (EPA) |
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| Properties | |
| C18H19NO4 | |
| Molar mass | 313.353 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
The biosynthesis of erysodienone involves a key step of oxidative phenol coupling. Starting with S-norprotosinomenine precursor A, cyclization via oxidative phenol coupling forms intermediate B, which in turn can be rearranged to form intermediate C. Hydrogenation of C forms the diphenoquinone intermediate E. An intramolecular Michael addition reaction converts E to the final product, erysodienone.[6]
Proposed biosynthetic pathway of erysodienone
A biomimetic synthesis route for erysodienone was developed based on a similar oxidative phenol coupling mechanism. Barton and co-workers[2] found that treating bisphenolethylamine precursor F with oxidants such as K3Fe(CN)6 initiated oxidative phenol coupling to form the 9-membered ring structure in intermediate D that itself undergo a Michael addition to give erysodienone.[7]
Biomimetic synthesis of erysodienone
