(+)-cis-Nemorensic acid was synthesized from a chiral Diels-Alder adduct prepared by a catalytic enantioselective Diels-Alder reaction with 2,5-dimethylfuran and 2,2,2-trifluoroethyl acrylate.
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Asymmetric synthesis of (+)-cis-nemorensic acid from a chiral Diels-Alder adduct of 2,5-dimethylfuran.
Chem Commun (Camb)
December 2007
Department of Chemistry, Sungkyunkwan University, Suwon 440-746, Korea.
(+)-cis-Nemorensic acid was synthesized from a chiral Diels-Alder adduct prepared by a catalytic enantioselective Diels-Alder reaction with 2,5-dimethylfuran and 2,2,2-trifluoroethyl acrylate.
View Article and Find Full Text PDFStereocontrolled syntheses of the nemorensic acids using 6-diazoheptane-2,5-dione in carbonyl ylide cycloadditions.
J Org Chem
December 2004
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, United Kingdom.
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 oxidative cleavage of the ring originally derived from the cyclic carbonyl ylide intermediate provides a straightforward access to polysubstituted tetrahydrofurans, and in particular an efficient entry to the nemorensic acids.
View Article and Find Full Text PDFUse of allene in 1,3-dipolar addition to a carbonyl ylide: syntheses of 3-hydroxy-cis-nemorensic acid and nemorensic acid.
Chem Commun (Camb)
April 2004
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UKOX1 3TA.
1,3-Dipolar addition of allene to the carbonyl ylide derived from 6-diazoheptane-2,5-dione is the key step in syntheses of 3-hydroxy-cis-nemorensic acid and nemorensic acid.
View Article and Find Full Text PDFOxidative cyclization based on reversing the polarity of enol ethers and ketene dithioacetals. Construction of a tetrahydrofuran ring and application to the synthesis of (+)-nemorensic Acid.
J Am Chem Soc
August 2002
Department of Chemistry, Washington University, St. Louis, Missouri 63130, USA.
The utility of oxidative cyclization reactions for the construction of tetrahydrofuran rings has been examined. In these experiments, alcohol nucleophiles were found to be effective traps for radical cation intermediates generated from both enol ether and ketene dithioacetal groups. The reactivity of the alcohol trapping group appeared to lie between that of an enol ether and an allylsilane trapping group.
View Article and Find Full Text PDFConcise, stereoselective syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid via tandem carbonyl ylide formation-cycloaddition.
Org Lett
May 2002
Dyson Perrins Laboratory, Department of Chemistry, University of Oxford, South Parks Road, OX1 3QY, UK.
[reaction: see text] 1,3-Dipolar cycloaddition of propargyl bromide with the carbonyl ylide derived from 6-diazoheptane-2,5-dione is the key step in concise syntheses of cis-nemorensic acid and 4-hydroxy-cis-nemorensic acid.
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