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Stereocontrolled syntheses of the nemorensic acids using 6-diazoheptane-2,5-dione in carbonyl ylide cycloadditions.

Abstract:

Levulinic acid-derived 6-diazoheptane-2,5-dione (9) serves as a common precursor in a formal synthesis of frontalin 19, and in syntheses of cis-nemorensic acid 1, 4-hydroxy-cis-nemorensic acid 2, 3-hydroxy-cis-nemorensic acid 3, and nemorensic acid 4. The key step in these syntheses is the Rh(2)(OAc)(4)-catalyzed tandem carbonyl ylide formation-intermolecular 1,3-dipolar cycloadditions of diazodione 9 with formaldehyde, alkynes or allene, which occur with high regioselectivity. Subsequent oxi...

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Publication status:
Published

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Publisher copy:
10.1021/jo048446b

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Le Strat, F More by this author
Donohue, AC More by this author
Brückl, T More by this author
Journal:
The Journal of organic chemistry
Volume:
69
Issue:
25
Pages:
8796-8803
Publication date:
2004-12-05
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:cf0a2e44-866a-41fc-8ad1-963f5931328e
Source identifiers:
32924
Local pid:
pubs:32924

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