An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine
Catechol derivatives directly bonded to all-carbon quaternary stereocentres are prevalent in nature. An oxidative coupling strategy for the synthesis of this motif is described. Pivoting on the base-catalysed Michael addition of carbon-centred pro-nucleophiles to in situ generated ortho-benzoquinone...
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| Format: | Conference item |
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2010
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| _version_ | 1797094491245510656 |
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| author | Bogle, K Hirst, D Dixon, D |
| author_facet | Bogle, K Hirst, D Dixon, D |
| author_sort | Bogle, K |
| collection | OXFORD |
| description | Catechol derivatives directly bonded to all-carbon quaternary stereocentres are prevalent in nature. An oxidative coupling strategy for the synthesis of this motif is described. Pivoting on the base-catalysed Michael addition of carbon-centred pro-nucleophiles to in situ generated ortho-benzoquinones, the method is broad in scope, high yielding and provides remarkably simple access to this challenging motif. The application of this methodology in the total synthesis of the crinane-type amaryllidaceae alkaloids (±)-powelline and (±)-buphanidrine is demonstrated and our efforts towards an enantioselective synthesis described. © 2010 Elsevier Ltd. |
| first_indexed | 2024-03-07T04:14:47Z |
| format | Conference item |
| id | oxford-uuid:c9110306-1653-4bee-b4e7-16b7d03f750a |
| institution | University of Oxford |
| last_indexed | 2024-03-07T04:14:47Z |
| publishDate | 2010 |
| record_format | dspace |
| spelling | oxford-uuid:c9110306-1653-4bee-b4e7-16b7d03f750a2022-03-27T06:56:17ZAn oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrineConference itemhttp://purl.org/coar/resource_type/c_5794uuid:c9110306-1653-4bee-b4e7-16b7d03f750aSymplectic Elements at Oxford2010Bogle, KHirst, DDixon, DCatechol derivatives directly bonded to all-carbon quaternary stereocentres are prevalent in nature. An oxidative coupling strategy for the synthesis of this motif is described. Pivoting on the base-catalysed Michael addition of carbon-centred pro-nucleophiles to in situ generated ortho-benzoquinones, the method is broad in scope, high yielding and provides remarkably simple access to this challenging motif. The application of this methodology in the total synthesis of the crinane-type amaryllidaceae alkaloids (±)-powelline and (±)-buphanidrine is demonstrated and our efforts towards an enantioselective synthesis described. © 2010 Elsevier Ltd. |
| spellingShingle | Bogle, K Hirst, D Dixon, D An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine |
| title | An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine |
| title_full | An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine |
| title_fullStr | An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine |
| title_full_unstemmed | An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine |
| title_short | An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine |
| title_sort | oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine |
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