Rapid assembly of highly-functionalised difluorinated cyclooctenones via ring-closing metathesis
Building block methodology from trifluoroethanol and ring-closing metathesis using a Furstner modification of Grubbs' conditions allows the rapid synthesis of novel difluorinated cyclooctenones.
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| Published in | Chemical communications (Cambridge, England) no. 3; pp. 228 - 229 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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CAMBRIDGE
Royal Soc Chemistry
07.02.2002
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| Abstract | Building block methodology from trifluoroethanol and ring-closing metathesis using a Furstner modification of Grubbs' conditions allows the rapid synthesis of novel difluorinated cyclooctenones. |
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| AbstractList | Building block methodology from trifluoroethanol and ring-closing metathesis using a Furstner modification of Grubbs' conditions allows the rapid synthesis of novel difluorinated cyclooctenones. Building block methodology from trifluoroethanol and ring-closing metathesis using a Fürstner modification of Grubbs' conditions allows the rapid synthesis of novel difluorinated cyclooctenones. |
| Author | Kariuki, BM Watson, M Thomas, AC Spencer, NS Percy, JM Pintat, S Smith, CA Owton, WM |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/12120378$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/ja001415n 10.1021/ol007047+ 10.1021/cr990407q 10.1021/jo0155761 10.1039/b004766j 10.1021/jo001549j 10.1021/jm0004897 |
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| Keywords | REARRANGEMENTS ONE-POT SYNTHESIS TRIFLUOROMETHYLTRIMETHYLSILANE ORGANOFLUORINE-ORGANOSILICON CHEMISTRY GLUCOSE ACYLSILANES |
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| References | Boyer, FD (WOS:000168911300066) 2001; 66 Schirlin, D (WOS:A1996BG35X00013) 1996; 639 Wang, W (WOS:000088347300010) 2000; 39 Harrington, PE (WOS:000080681400041) 1999; 64 PATEL, ST (WOS:A1995RP10100024) 1995; 51 Patel, ST (WOS:A1996TQ14600028) 1996; 61 Furstner, A (WOS:000089227800002) 2000; 39 Balnaves, AS (WOS:000082423200021) 1999 Wolfe, MS (WOS:000169367000001) 2001; 44 van Hooft, PAV (WOS:000167322700023) 2001; 3 GELB, MH (WOS:A1985AGF5000001) 1985; 24 Lefebvre, O (WOS:000073579100012) 1998; 54 Lefebvre, O (WOS:000167630500003) 2001; 66 Yet, L (WOS:000088838500010) 2000; 100 Hyldtoft, L (WOS:000089285300013) 2000; 122 Furstner, A (WOS:A1997XY93800007) 1997; 119 Broadhurst, MJ (WOS:000089855200008) 2000 KUROBOSHI, M (WOS:A1990DB89100036) 1990; 63 Dimartino, G (WOS:000083995100044) 1999 |
| References_xml | – start-page: 2535 year: 1999 ident: WOS:000083995100044 article-title: Oxy-Cope rearrangements of fluorinated divinylcyclohexanols: a modular method for the construction of selectively fluorinated cyclic ketones publication-title: CHEMICAL COMMUNICATIONS contributor: fullname: Dimartino, G – volume: 122 start-page: 8444 year: 2000 ident: WOS:000089285300013 article-title: Carbohydrate carbocyclization by a novel zinc-mediated domino reaction and ring-closing olefin metathesis publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja001415n contributor: fullname: Hyldtoft, L – volume: 119 start-page: 9130 year: 1997 ident: WOS:A1997XY93800007 article-title: Total syntheses of (+)-ricinelaidic acid lactone and of (-)-gloeosporone based on transition-metal-catalyzed C-C bond formations publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Furstner, A – volume: 3 start-page: 731 year: 2001 ident: WOS:000167322700023 article-title: Stereoselective transformations on D-glucose-derived eight-membered ring carbocycles publication-title: ORGANIC LETTERS doi: 10.1021/ol007047+ contributor: fullname: van Hooft, PAV – volume: 100 start-page: 2963 year: 2000 ident: WOS:000088838500010 article-title: Metal-mediated synthesis of medium-sized rings publication-title: CHEMICAL REVIEWS doi: 10.1021/cr990407q contributor: fullname: Yet, L – volume: 66 start-page: 4094 year: 2001 ident: WOS:000168911300066 article-title: From carbohydrates to polyoxygenated cyclooctenes via ring-closing metathesis publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo0155761 contributor: fullname: Boyer, FD – volume: 64 start-page: 4025 year: 1999 ident: WOS:000080681400041 article-title: Difluorocyclopentenone synthesis publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Harrington, PE – start-page: 3217 year: 2000 ident: WOS:000089855200008 article-title: Synthesis of alpha-hydroxy-beta,beta-difluoro-gamma-ketoesters via [3,3]sigmatropic rearrangements publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 doi: 10.1039/b004766j contributor: fullname: Broadhurst, MJ – volume: 63 start-page: 1185 year: 1990 ident: WOS:A1990DB89100036 article-title: DIASTEREOSELECTIVE REDUCTION OF ALPHA,ALPHA-DIFLUORO BETA-HYDROXY KETONES TO SYN-2,2-DIFLUORO-1,3-DIOLS AND ANTI-2,2-DIFLUORO-1,3-DIOLS publication-title: BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN contributor: fullname: KUROBOSHI, M – volume: 54 start-page: 5939 year: 1998 ident: WOS:000073579100012 article-title: Mixed organofluorine-organosilicon chemistry. 8. One-pot synthesis of 2,2-difluoro-1,5 diketones from acylsilanes, trifluoromethyltrimethylsilane and enones, and their annulation reaction publication-title: TETRAHEDRON contributor: fullname: Lefebvre, O – volume: 61 start-page: 166 year: 1996 ident: WOS:A1996TQ14600028 article-title: [2,3]-Wittig rearrangements of difluoroallylic ethers. A facile entry to highly functionalized molecules containing a CF2 group publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: Patel, ST – volume: 66 start-page: 1941 year: 2001 ident: WOS:000167630500003 article-title: Mixed organofluorine-organosilicon chemistry. 13. One-pot synthesis of difluoroaldols from acylsilanes and trifluoromethyltrimethylsilane. Application to the synthesis of a difluoro analogue of egomaketone publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo001549j contributor: fullname: Lefebvre, O – volume: 51 start-page: 9201 year: 1995 ident: WOS:A1995RP10100024 article-title: NEW FLUORINE-CONTAINING BUILDING-BLOCKS FROM TRIFLUOROETHANOL .1. publication-title: TETRAHEDRON contributor: fullname: PATEL, ST – start-page: 2525 year: 1999 ident: WOS:000082423200021 article-title: The generation of difluoroenolates from trifluoroethanol and reproducible syntheses of alpha,alpha-difluoro-beta-hydroxy ketones publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 contributor: fullname: Balnaves, AS – volume: 39 start-page: 3012 year: 2000 ident: WOS:000089227800002 article-title: Olefin metathesis and beyond publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Furstner, A – volume: 39 start-page: 2466 year: 2000 ident: WOS:000088347300010 article-title: From glucose to cyclooctanic carbaglucose: A new class of carbohydrate mimetics publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Wang, W – volume: 24 start-page: 1813 year: 1985 ident: WOS:A1985AGF5000001 article-title: FLUORO KETONE INHIBITORS OF HYDROLYTIC ENZYMES publication-title: BIOCHEMISTRY contributor: fullname: GELB, MH – volume: 639 start-page: 169 year: 1996 ident: WOS:A1996BG35X00013 article-title: Elucidation of the mechanism of inhibition of human immunodeficiency virus 1 protease by difluorostatones publication-title: BIOMEDICAL FRONTIERS OF FLUORINE CHEMISTRY contributor: fullname: Schirlin, D – volume: 44 start-page: 2039 year: 2001 ident: WOS:000169367000001 article-title: Secretase targets for Alzheimer's disease: Identification and therapeutic potential publication-title: JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1021/jm0004897 contributor: fullname: Wolfe, MS |
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| Title | Rapid assembly of highly-functionalised difluorinated cyclooctenones via ring-closing metathesis |
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