A novel carbocyclic ring closure of hex-5-enopyranosides and pent-4-enofuranosides
Nitrile oxide cycloadditions to hex-5-enopyranosides and pent-4-enofuranosides give spiroisoxazolines, which upon reductive opening of the heterocyclic ring undergo spontaneous intramolecular aldol-like condensation to give six- and five-membered densely functionalised carbocycles.
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| Published in | Synlett no. 8; pp. 1289 - 1291 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
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Thieme Medical Publishers
01.08.1999
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| Abstract | Nitrile oxide cycloadditions to hex-5-enopyranosides and pent-4-enofuranosides give spiroisoxazolines, which upon reductive opening of the heterocyclic ring undergo spontaneous intramolecular aldol-like condensation to give six- and five-membered densely functionalised carbocycles. |
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| AbstractList | Nitrile oxide cycloadditions to hex-5-enopyranosides and pent-4-enofuranosides give spiroisoxazolines, which upon reductive opening of the heterocyclic ring undergo spontaneous intramolecular aldol-like condensation to give six- and five-membered densely functionalised carbocycles. |
| Author | Koftis, TV Gallos, JK Moutsos Koumbis, AE |
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| Keywords | carbohydrates ROUTE carbocycles CONVERSION D-RIBOSE SUGARS hydrogenation enaminones REARRANGEMENT FREE-RADICAL CYCLIZATIONS CYCLOADDITION CYCLOHEXANONES nitrile oxides CARBOHYDRATE-DERIVATIVES |
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| References | Martinez-Grau, A (WOS:000072909400007) 1998; 27 Sellier, O (WOS:000078170400010) 1999; 40 Marco-Contelles, J (WOS:000075020700001) 1998 FERRIER, RJ (WOS:A1979HA17000015) 1979 Gallos, JK (WOS:A1997XW07800004) 1997 MUKAIYAMA, T (WOS:A1960WB34700017) 1960; 82 Gothelf, KV (WOS:000073091500013) 1998; 98 Chretien, F (WOS:A1997XR68900020) 1997; 38 Sollogoub, M (WOS:000073490400032) 1998; 39 FERRIER, RJ (WOS:A1993MN94100008) 1993; 93 OHIRA, S (WOS:A1995QK51800043) 1995; 36 FraserReid, B (WOS:A1996TV82800001) 1996; 29 Berecibar, A (WOS:000079240100005) 1999; 99 Cere, V (WOS:A1997YD72700043) 1997; 38 Iimori, T (WOS:A1996TT06200025) 1996; 37 MUKAI, C (WOS:A1995RN50500027) 1995; 36 Zhuo, JC (WOS:000075347800002) 1998; 36 GALLOS, JK (WOS:A1994NC13800001) 1994 Sudha, AVRL (WOS:000073297800034) 1998 ITO, H (WOS:A1993LZ13300045) 1993; 115 Das, SK (WOS:A1997WV55600009) 1997; 36 HASSNER, A (WOS:A1990EA83700023) 1990; 55 Ovaa, H (WOS:000073235800041) 1998; 39 HILL, JM (WOS:A1994NQ34000020) 1994 BOA, AN (WOS:A1993LJ55800002) 1993 CURRAN DP (WOS:000082147000035.5) 1988; 1 Gallos, JK (WOS:A1997XW07800005) 1997 |
| References_xml | – start-page: 1277 year: 1993 ident: WOS:A1993LJ55800002 article-title: CYCLOADDITION OF NITRILE OXIDES TO HOMOCHIRAL VINYL ETHERS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: BOA, AN – volume: 93 start-page: 2779 year: 1993 ident: WOS:A1993MN94100008 article-title: THE CONVERSION OF CARBOHYDRATE-DERIVATIVES INTO FUNCTIONALIZED CYCLOHEXANES AND CYCLOPENTANES publication-title: CHEMICAL REVIEWS contributor: fullname: FERRIER, RJ – volume: 99 start-page: 779 year: 1999 ident: WOS:000079240100005 article-title: Synthesis and biological activity of natural aminocyclopentitol glycosidase inhibitors: Mannostatins, trehazolin, allosamidins, and their analogues publication-title: CHEMICAL REVIEWS contributor: fullname: Berecibar, A – volume: 1 start-page: 129 year: 1988 ident: WOS:000082147000035.5 publication-title: ADV CYCLOADDITION contributor: fullname: CURRAN DP – start-page: 1455 year: 1979 ident: WOS:A1979HA17000015 article-title: UNSATURATED CARBOHYDRATES .21. CARBOCYCLIC RING-CLOSURE OF A HEX-5-ENOPYRANOSIDE DERIVATIVE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: FERRIER, RJ – volume: 98 start-page: 863 year: 1998 ident: WOS:000073091500013 article-title: Asymmetric 1,3-dipolar cycloaddition reactions publication-title: CHEMICAL REVIEWS contributor: fullname: Gothelf, KV – volume: 55 start-page: 5505 year: 1990 ident: WOS:A1990EA83700023 article-title: CYCLOADDITIONS .44. A 2-STEP CONVERSION OF CARBONYL-COMPOUNDS INTO FUNCTIONALIZED 5-MEMBERED AND 6-MEMBERED RING THIOETHERS VIA INTRAMOLECULAR CYCLOADDITION publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: HASSNER, A – volume: 40 start-page: 853 year: 1999 ident: WOS:000078170400010 article-title: Ring closing metathesis as an efficient approach to branched cyclitols and aminocyclitols: a short synthesis of valiolamine publication-title: TETRAHEDRON LETTERS contributor: fullname: Sellier, O – volume: 37 start-page: 649 year: 1996 ident: WOS:A1996TT06200025 article-title: Palladium chloride mediated rearrangement of 6-deoxyhex-5-enopyranosides into cyclohexanones publication-title: TETRAHEDRON LETTERS contributor: fullname: Iimori, T – volume: 36 start-page: 493 year: 1997 ident: WOS:A1997WV55600009 article-title: Novel carbocyclic ring closure of hex-5-enopyranosides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH contributor: fullname: Das, SK – volume: 29 start-page: 57 year: 1996 ident: WOS:A1996TV82800001 article-title: Some progeny of 2,3-unsaturated sugars - They little resemble grandfather glucose: Twenty years later publication-title: ACCOUNTS OF CHEMICAL RESEARCH contributor: fullname: FraserReid, B – volume: 38 start-page: 5977 year: 1997 ident: WOS:A1997XR68900020 article-title: A unified strategy for the synthesis of enantiomerically pure branched-chain cyclohexenones and -cyclopentenones from a single progenitor publication-title: TETRAHEDRON LETTERS contributor: fullname: Chretien, F – start-page: 925 year: 1998 ident: WOS:000073297800034 article-title: Carbohydrates to carbocycles: an expedient synthesis of pseudo-sugars publication-title: CHEMICAL COMMUNICATIONS contributor: fullname: Sudha, AVRL – volume: 36 start-page: 5761 year: 1995 ident: WOS:A1995RN50500027 article-title: A HIGHLY DIASTEREOSELECTIVE CONSTRUCTION OF OPTICALLY-ACTIVE BICYCLO[3.3.0]OCTENONE DERIVATIVES FROM L-ASCORBIC-ACID VIA PAUSON-KHAND REACTION publication-title: TETRAHEDRON LETTERS contributor: fullname: MUKAI, C – volume: 115 start-page: 8835 year: 1993 ident: WOS:A1993LZ13300045 article-title: ZIRCONIUM-MEDIATED, HIGHLY DIASTEREOSELECTIVE RING CONTRACTION OF CARBOHYDRATE-DERIVATIVES - SYNTHESIS OF HIGHLY FUNCTIONALIZED, ENANTIOMERICALLY PURE CARBOCYCLES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: ITO, H – volume: 39 start-page: 3471 year: 1998 ident: WOS:000073490400032 article-title: Titanium (IV) promoted rearrangement of 6-deoxy-hex-5-enopyranosides into cyclohexanones publication-title: TETRAHEDRON LETTERS contributor: fullname: Sollogoub, M – volume: 82 start-page: 5339 year: 1960 ident: WOS:A1960WB34700017 article-title: THE REACTIONS OF PRIMARY NITROPARAFFINS WITH ISOCYANATES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: MUKAIYAMA, T – volume: 39 start-page: 3025 year: 1998 ident: WOS:000073235800041 article-title: An expeditious route to the synthesis of highly functionalized chiral oxepines from monosaccharides publication-title: TETRAHEDRON LETTERS contributor: fullname: Ovaa, H – volume: 38 start-page: 7797 year: 1997 ident: WOS:A1997YD72700043 article-title: New simple and inexpensive synthetic route, mediated by sulfur, to enantiopure (-)-conduritol E derivative from D-mannitol. publication-title: TETRAHEDRON LETTERS contributor: fullname: Cere, V – start-page: 693 year: 1998 ident: WOS:000075020700001 article-title: Carbocycles from carbohydrates via free radical cyclizations: Synthesis and manipulation of annulated furanoses publication-title: SYNLETT contributor: fullname: Marco-Contelles, J – start-page: 2457 year: 1997 ident: WOS:A1997XW07800004 article-title: Highly diastereoselective synthesis of densely functionalized cyclopentanoids by intramolecular azomethine imine cycloadditions in sugar templates publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: Gallos, JK – volume: 27 start-page: 155 year: 1998 ident: WOS:000072909400007 article-title: Carbocycles from carbohydrates via free radical cyclizations: new synthetic approaches to glycomimetics publication-title: CHEMICAL SOCIETY REVIEWS contributor: fullname: Martinez-Grau, A – start-page: 2461 year: 1997 ident: WOS:A1997XW07800005 article-title: Synthesis of cyclitols fused with a furoxan ring from alditols by intramolecular nitrile oxide dimerization publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: Gallos, JK – volume: 36 start-page: 565 year: 1998 ident: WOS:000075347800002 article-title: NMR of enaminones - Part 8 - H-1, C-13 and O-17 NMR spectra of primary and secondary 1,2-disubstituted enaminones: configuration, conformation and intramolecular hydrogen bonding publication-title: MAGNETIC RESONANCE IN CHEMISTRY contributor: fullname: Zhuo, JC – start-page: 611 year: 1994 ident: WOS:A1994NC13800001 article-title: SYNTHESIS OF ENANTIOMERICALLY PURE BICYCLO[3.1.0]HEXANES FROM D-RIBOSE BY INTRAMOLECULAR CYCLOPROPANATION publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: GALLOS, JK – start-page: 1483 year: 1994 ident: WOS:A1994NQ34000020 article-title: PREPARATION OF NEPLANOCIN-A FROM D-RIBOSE AND BY A CHEMOENZYMIC METHOD publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: HILL, JM – volume: 36 start-page: 1537 year: 1995 ident: WOS:A1995QK51800043 article-title: SYNTHESIS OF (-)-NEPLANOCIN-A VIA C-H INSERTION OF ALKYLIDENECARBENE publication-title: TETRAHEDRON LETTERS contributor: fullname: OHIRA, S |
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| Snippet | Nitrile oxide cycloadditions to hex-5-enopyranosides and pent-4-enofuranosides give spiroisoxazolines, which upon reductive opening of the heterocyclic ring... |
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| Title | A novel carbocyclic ring closure of hex-5-enopyranosides and pent-4-enofuranosides |
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