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An oxidative coupling for the synthesis of arylated quaternary stereocentres and its application in the total synthesis of powelline and buphanidrine

Abstract:

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 amaryl...

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Publication status:
Published

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Publisher copy:
10.1016/j.tet.2010.04.132

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Host title:
TETRAHEDRON
Volume:
66
Issue:
33
Pages:
6399-6410
Publication date:
2010-08-14
DOI:
ISSN:
0040-4020
Keywords:
Pubs id:
pubs:67556
UUID:
uuid:c9110306-1653-4bee-b4e7-16b7d03f750a
Local pid:
pubs:67556
Source identifiers:
67556
Deposit date:
2012-12-19

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