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Intramolecular oxonium ylide formation-[2,3] sigmatropic rearrangement of diazocarbonyl-substituted cyclic unsaturated acetals: a formal synthesis of hyperolactone C.

Abstract:

Rh(II)-catalyzed oxonium ylide formation-[2,3] sigmatropic rearrangement of α-diazo-β-ketoesters possessing γ-cyclic unsaturated acetal substitution, followed by acid-catalyzed elimination-lactonization, provides a concise approach to 1,7-dioxaspiro[4.4]non-2-ene-4,6-diones. The process creates adjacent quaternary stereocenters with full control of the relative stereochemistry. An unsymmetrical monomethylated cyclic unsaturated acetal leads to hyperolactone C, where ylide formation-rearrangem...

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Publication status:
Published

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Publisher copy:
10.1021/jo501893r

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
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Publisher:
American Chemical Society
Journal:
The Journal of organic chemistry
Volume:
79
Issue:
20
Pages:
9728-9734
Publication date:
2014-10-05
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:df2e4027-ee49-4001-b390-5656d0bde933
Source identifiers:
486001
Local pid:
pubs:486001
Language:
English

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