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Anomeric oxygen to carbon rearrangements of alkynyl tributylstannane derivatives of furanyl (gamma)- and pyranyl (delta)-lactols.

Abstract:

Tetrahydropyran and tetrahydrofuran containing natural products, drugs and agrochemicals often possess carbon-carbon bonds adjacent to the heteroatom. Consequently, new methods for the construction of anomeric carbon-carbon bonds are of considerable importance. We have devised a new strategy to access these systems that requires the treatment of O-glycoside alkynyl tributylstannane derivatives of furanyl and pyranyl lactols with Lewis acid to effect oxygen to carbon rearrangements. This leads...

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Publication status:
Published

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Publisher copy:
10.1039/b316858a

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Institution:
University of Oxford
Division:
MPLS
Department:
Chemistry
Sub department:
Organic Chemistry
Role:
Author
Journal:
Organic and biomolecular chemistry
Volume:
2
Issue:
8
Pages:
1145-1154
Publication date:
2004-04-01
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
Source identifiers:
52057
Language:
English
Keywords:
Pubs id:
pubs:52057
UUID:
uuid:13e9ccb7-7dac-41c7-9392-6af9da8f07d5
Local pid:
pubs:52057
Deposit date:
2012-12-19

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