Concerning the reaction of anti-benzene dioxide with various nucleophiles

Esser, Thomas; Farkas, F.; Mangholz, Sissi E.; Séquin, Urs

doi:10.1016/s0040-4020(01)90392-8

Cited by 7 publications

(6 citation statements)

References 18 publications

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“…Racemic conduritol B tetraacetate (±)‐ 36 was obtained using a modification (Scheme ) of the method reported by Guo et al26 Guo et al had reported that the diacetoxy‐dibromide 35 b , available from p ‐benzoquinone in three steps, could be converted to (±)‐ 36 a by heating with potassium acetate and acetic anhydride in refluxing acetic acid. We found that 35 b could be generated in situ by adding potassium carbonate to a suspension of the diol‐dibromide 35 a 30, 31 in acetic anhydride. Addition of acetic acid to this mixture followed by warming to reflux then led to formation of (±)‐ 36 .…”

Section: Resultsmentioning

confidence: 99%

Asymmetric Induction of Conduritols via AAA Reactions: Synthesis of the Aminocyclohexitol of Hygromycin A

2001

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Two synthetic routes towards the construction of the aminocyclohexitol moiety of hygromycin A have been developed based on palladium-catalyzed asymmetric alkylation of conduritol derivatives. A protocol has been established whereby this biologically relevant molecule is formed from benzoquinone. A conduritol A derivative is synthesized in eight steps from benzoquinone and is then subjected to the palladium reaction. From this flexible intermediate, four epimers of the aminocyclitol, including the natural one, can be obtained with complete stereoselectivity. Racemic conduritol B derivatives are available in four steps from benzoquinone, and these are then made enantiomerically pure by a palladium-catalyzed dynamic kinetic resolution. From the chiral conduritol B, the aminocyclitol is available in six steps. Excellent levels of enantio- and diastereoselectivity highlight these strategies.

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Section: Resultsmentioning

confidence: 99%

Asymmetric Induction of Conduritols via AAA Reactions: Synthesis of the Aminocyclohexitol of Hygromycin A

2001

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“…For this analysis, 3a was converted into the corresponding diacetate 2a with pyridine and acetic anhydride. Treatment of diol 3a with potassium hydroxide and powdered molecular sieves in tetrahydrofuran, a slight modification of Farkas's method, 29 However, by addition of limited amounts of ethanol to the reaction mixture, complete reaction to 4b could be achieved in less than 30 min (H.-J. Altenbach and A. Kaffee, unpublished results).…”

Section: Resultsmentioning

confidence: 99%

“…For this analysis, 3a was converted into the corresponding diacetate 2a with pyridine and acetic anhydride. Treatment of diol 3a with potassium hydroxide and powdered molecular sieves in tetrahydrofuran, a slight modification of Farkas's method, leads to anti -benzene dioxide ( trans -1,2:3,4-diepoxycyclohex-5-ene) 4a in good yields. Conversion of the diacetate 2b under the same conditions was unsatisfactory.…”

Section: Resultsmentioning

confidence: 99%

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Enzyme-Assisted Total Synthesis of the Optical Antipodes d-myo-Inositol 3,4,5-Trisphosphate and d-myo-Inositol 1,5,6-Trisphosphate: Aspects of Their Structure−Activity Relationship to Biologically Active Inositol Phosphates

et al. 1999

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Unambiguous total syntheses of both optical antipodes of the enantiomeric pair D-myo-inositol 3,4,5-trisphosphate (Ins(3,4,5)P3) and D-myo-inositol 1,5,6-trisphosphate (Ins(1,5,6)P3) are described. The ring system characteristic of myo-inositol was constructed de novo from p-benzoquinone. X-ray data for the enzymatically resolved (1S,2R,3R,4S)-1,4-diacetoxy-2,3-dibromocyclohex-5-ene enabled the unequivocal assignment of the absolute configuration. Subsequent transformations under stereocontrolled conditions led to enantiopure C2-symmetrical 1,4-(di-O-benzyldiphospho)conduritol B derivatives. Their synthetic potential was exploited to prepare Ins(3,4,5,6)P4 and Ins(1,4,5,6)P4 in three steps. With a recently identified and partially purified InsP5/InsP4 phosphohydrolase from Dictyostelium discoideum, these enantiomers could be converted to the target compounds, Ins(3,4,5)P3 and Ins(1,5,6)P3, on a preparative scale. An HPLC system employed for both purification of the inositol phosphates and analytical runs ensured that the products were isomerically homogeneous. The sensitivity of detection achieved by a complexometric postcolumn derivatization method indicates that the complexation properties of Ins(3,4,5)P3/Ins(1,5,6)P3 resemble those of Ins(1,2,3)P3, a compound with antioxidant potential. The set of inositol phosphates synthesized was used to clarify structural motifs important for molecular recognition by p42(IP4), a high-affinity Ins(1,3,4,5)P4/PtdIns(3,4,5)P3-specific binding protein from pig cerebellum.

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“…1 H and 13 C NMR spectra, and melting point range (not reported) are in accordance with literature data. 20 4.5. Synthesis of (1R,2S,3S,4S)/(1S,2R,3R,4R)-1-cyano-3,4-epoxy-2-trimethylsilylcyclohex-1-ene, (±)-5…”

Section: 2mentioning

confidence: 99%

Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4

D’Antona

Nicolosi

Morrone

et al. 2010

Tetrahedron: Asymmetry

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Concerning the reaction of anti-benzene dioxide with various nucleophiles

Cited by 7 publications

References 18 publications

Asymmetric Induction of Conduritols via AAA Reactions: Synthesis of the Aminocyclohexitol of Hygromycin A

Asymmetric Induction of Conduritols via AAA Reactions: Synthesis of the Aminocyclohexitol of Hygromycin A

Enzyme-Assisted Total Synthesis of the Optical Antipodes d-myo-Inositol 3,4,5-Trisphosphate and d-myo-Inositol 1,5,6-Trisphosphate: Aspects of Their Structure−Activity Relationship to Biologically Active Inositol Phosphates

Synthesis of novel cyano-cyclitols and their stereoselective biotransformation catalyzed by Rhodococcus erythropolis A4

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