Chemistry of tricarbonyl hemiketals and application of Evans technology to the total synthesis of the immunosuppressant (-)-FK-506
Details of model studies probing the chemistry of the tricarbonyl region of FK-506 are presented, and their use in designing a successful route to this immunosuppressant is outlined. Applications of asymmetric oxazolidinone alkylation/aldol methodology to a convergent, highly flexible synthesis of t...
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| Published in | Journal of the American Chemical Society Vol. 112; no. 8; pp. 2998 - 3017 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
01.04.1990
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Details of model studies probing the chemistry of the tricarbonyl region of FK-506 are presented, and their use in designing a successful route to this immunosuppressant is outlined. Applications of asymmetric oxazolidinone alkylation/aldol methodology to a convergent, highly flexible synthesis of the C10-C18 fragment and to improvements in the preparation of the C20-C34 segment are also discussed. |
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| AbstractList | Details of model studies probing the chemistry of the tricarbonyl region of FK-506 are presented, and their use in designing a successful route to this immunosuppressant is outlined. Applications of asymmetric oxazolidinone alkylation/aldol methodology to a convergent, highly flexible synthesis of the C10-C18 fragment and to improvements in the preparation of the C20-C34 segment are also discussed. |
| Author | Jones, Todd K Desmond, Richard Reamer, Robert A Mills, Sander G |
| Author_xml | – sequence: 1 givenname: Todd K surname: Jones fullname: Jones, Todd K – sequence: 2 givenname: Robert A surname: Reamer fullname: Reamer, Robert A – sequence: 3 givenname: Richard surname: Desmond fullname: Desmond, Richard – sequence: 4 givenname: Sander G surname: Mills fullname: Mills, Sander G |
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| References_xml | – volume: 30 start-page: 919 year: 1989 ident: WOS:A1989T545000006 article-title: STUDIES DIRECTED TOWARDS THE TOTAL SYNTHESIS OF FK-506 - PREPARATION OF A C(1) TO C(15) SEGMENT publication-title: TETRAHEDRON LETTERS contributor: fullname: IRELAND, RE – volume: 50 start-page: 2198 year: 1985 ident: WOS:A1985AKG5400041 article-title: APPLICATION OF THE SWERN OXIDATION TO THE MANIPULATION OF HIGHLY REACTIVE CARBONYL-COMPOUNDS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: IRELAND, RE – volume: 54 start-page: 12 year: 1989 ident: WOS:A1989R739100007 article-title: STEREOSELECTIVE SYNTHESES OF FK-506 SUBUNITS BY THE RHODIUM(I)-CATALYZED HYDROGENATION OF DIENES - THE SYNTHESIS AND COUPLING OF A C-10-C-19 FRAGMENT publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: VILLALOBOS, A – volume: 54 start-page: 9 year: 1989 ident: WOS:A1989R739100005 article-title: STUDIES RELATING TO THE SYNTHESIS OF THE IMMUNOSUPPRESSIVE AGENT FK-506 - SYNTHESIS OF THE CYCLOHEXYL MOIETY VIA A GROUP-SELECTIVE EPOXIDATION publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: SCHREIBER, SL – volume: 45 start-page: 4323 year: 1978 ident: WOS:A1990CY82600023.17 publication-title: TETRAHEDRON LETT contributor: fullname: DUGGAN AJ – volume: 54 start-page: 17 year: 1989 ident: WOS:A1989R739100009 article-title: STUDIES RELATING TO THE SYNTHESIS OF THE IMMUNOSUPPRESSIVE AGENT FK-506 - COUPLING OF FRAGMENTS VIA A STEREOSELECTIVE TRISUBSTITUTED OLEFIN FORMING REACTION SEQUENCE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: JONES, AB – year: 1986 ident: WOS:A1990CY82600023.51 publication-title: THESIS HARVARD U contributor: fullname: SJOGREN EB – volume: 54 start-page: 11 year: 1989 ident: WOS:A1989R739100006 article-title: SYNTHETIC ROUTE TO THE TRICARBONYL REGION OF FK-506 publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: EGBERTSON, M – volume: 39 start-page: 1490 year: 1974 ident: WOS:A1974T150500008 article-title: CYCLIC PHENYLBORONATES AS HYDROXYL PROTECTING GROUPS IN SYNTHESIS OF MONOESTERS OF MACROLIDE AGLYCONES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: PERUN, TJ – volume: 54 start-page: 15 year: 1989 ident: WOS:A1989R739100008 article-title: STUDIES RELATING TO THE SYNTHESIS OF THE IMMUNOSUPPRESSIVE AGENT FK-506 - APPLICATION OF THE 2-DIRECTIONAL CHAIN SYNTHESIS STRATEGY TO THE PYRANOSE MOIETY publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: SCHREIBER, SL – volume: 30 start-page: 5235 year: 1989 ident: WOS:A1989AV45300012 article-title: ENANTIOSELECTIVE SYNTHESIS OF THE C(18)-C(35) SEGMENT OF IMMUNOSUPPRESSANT FK-506 USING EFFICIENT NEW METHODOLOGY publication-title: TETRAHEDRON LETTERS contributor: fullname: COREY, EJ – volume: 52 start-page: 4851 year: 1987 ident: WOS:A1987K713700005 article-title: OXIDATION OF VICINAL DIOLS TO ALPHA-DICARBONYL COMPOUNDS BY TRIFLUOROACETIC-ANHYDRIDE ACTIVATED DIMETHYLSULFOXIDE publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: AMON, CM – volume: 103 start-page: 2127 year: 1981 ident: WOS:A1981LM32700057 article-title: ENANTIOSELECTIVE ALDOL CONDENSATIONS .2. 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A SYNTHESIS OF ASCIDIACYCLAMIDE, A CYTO-TOXIC CYCLIC PEPTIDE FROM ASCIDIAN - DETERMINATION OF ITS ABSOLUTE-CONFIGURATION publication-title: TETRAHEDRON LETTERS contributor: fullname: HAMADA, Y |
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| Snippet | Details of model studies probing the chemistry of the tricarbonyl region of FK-506 are presented, and their use in designing a successful route to this... |
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| SubjectTerms | Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
| Title | Chemistry of tricarbonyl hemiketals and application of Evans technology to the total synthesis of the immunosuppressant (-)-FK-506 |
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