Investigations into a Biomimetic Approach toward CP-225,917 and CP-263,114
A biosynthesis of the structurally complex nonadride CP-225,917 (1) is outlined. A key step in this proposal is the dimerization of a C16 anhydride derived from the condensation of lauric acid and oxaloacetic acid. An important element of this step is a templating effect imposed by two thioester lin...
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| Published in | Journal of organic chemistry Vol. 65; no. 2; pp. 337 - 342 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
28.01.2000
Amer Chemical Soc |
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| Abstract | A biosynthesis of the structurally complex nonadride CP-225,917 (1) is outlined. A key step in this proposal is the dimerization of a C16 anhydride derived from the condensation of lauric acid and oxaloacetic acid. An important element of this step is a templating effect imposed by two thioester linkages, reminiscent of a polyketide or fatty acid synthase pathway. On the basis of this principle, the dimerization of two C11 anhydrides, templated by a 1,n-diol tether, leading to the core structure of CP-225,917 and CP-263,114 was investigated. |
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| AbstractList | A biosynthesis of the structurally complex nonadride CP-225,917 (1) is outlined. A key step in this proposal is the dimerization of a C16 anhydride derived from the condensation of lauric acid and oxaloacetic acid. An important element of this step is a templating effect imposed by two thioester linkages, reminiscent of a polyketide or fatty acid synthase pathway. On the basis of this principle, the dimerization of two C11 anhydrides, templated by a 1,n-diol tether, leading to the core structure of CP-225,917 and CP-263,114 was investigated. A biosynthesis of the structurally complex nonadride CP-225,917 (1) is outlined. A key step in this proposal is the dimerization of a C(16) anhydride derived from the condensation of lauric acid and oxaloacetic acid. An important element of this step is a templating effect imposed by two thioester linkages, reminiscent of a polyketide or fatty acid synthase pathway. On the basis of this principle, the dimerization of two C(11) anhydrides, templated by a 1,n-diol tether, leading to the core structure of CP-225,917 and CP-263,114 was investigated. |
| Author | Corbett, R. Michael Sulikowski, Gary A Agnelli, Fabio |
| Author_xml | – sequence: 1 givenname: Gary A surname: Sulikowski fullname: Sulikowski, Gary A – sequence: 2 givenname: Fabio surname: Agnelli fullname: Agnelli, Fabio – sequence: 3 givenname: R. Michael surname: Corbett fullname: Corbett, R. Michael |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/10813939$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.7164/antibiotics.50.1 10.1016/S0040-4039(98)01236-2 10.1016/0022-328X(89)87059-7 10.1016/S0040-4020(99)00360-9 10.1021/ja961000v 10.1002/(SICI)1521-3773(19990215)38:4<552::AID-ANIE552>3.0.CO;2-B 10.1002/(SICI)1521-3773(19980803)37:13/14<1882::AID-ANIE1882>3.0.CO;2-U 10.1016/S0040-4039(98)01978-9 10.1007/BF02172243 10.1021/ar00078a003 10.1002/anie.199728231 10.1002/anie.199711961 |
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| Keywords | CORE UNIDENTIFIED FUNGUS RAS FARNESYLATION INHIBITORS |
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| References | Nicolaou, KC (WOS:000078704200029) 1999; 38 Nicolaou, KC (WOS:000071469300038) 1997; 36 Sgarbi, PWM (WOS:A1997YG75800013) 1997 Waizumi, N (WOS:000075041200038) 1998; 39 Meng, DF (WOS:000080448400036) 1999; 38 Dabrah, TT (WOS:A1997WJ09700011) 1997; 119 Bio, MM (WOS:000078471800049) 1999; 121 Agnelli, F (WOS:000076995300016) 1998; 39 HUFF RK (WOS:000084905400010.16) 1972; 20 Nicolaou, KC (WOS:000080694400033) 1999; 38 ORSINI, F (WOS:A1989U779900012) 1989; 367 BARTON, DHR (WOS:A19656270700032) 1965 Nicolaou, KC (WOS:A1997XJ96000014) 1997; 36 Baldwin, JE (WOS:000080579800021) 1999; 55 Dabrah, TT (WOS:A1997WE84800001) 1997; 50 BARTON, DHR (WOS:A19656270700033) 1965 BALDWIN, J E (MEDLINE:13864341) 1962; 18 HUFF, RK (WOS:A1968B907500037) 1968 Kwon, OY (WOS:000075330000021) 1998; 37 SUTHERLAND, JK (WOS:A1967A249500004) 1967; 25 BARTON DH (WOS:000084905400010.7) 1996 SUZUKI, A (WOS:A1982NX81200004) 1982; 15 BLOOMER, JL (WOS:A1968A718600025) 1968 Armstrong, A (WOS:000074207500034) 1998 MOPPETT, CE (WOS:A19668460800007) 1966 Kwon, OY (WOS:000075330000020) 1998; 37 Chen, C (WOS:000076666800038) 1998; 120 DEWICK PM (WOS:000084905400010.14) 1997 Clive, DLJ (WOS:000080742600002) 1999; 40 Nicolaou, KC (WOS:000080694400034) 1999; 38 Armstrong A. (jo9911286b00004/jo9911286b00004_1) 1998; 552 Barton D. H. R. (jo9911286b00003/jo9911286b00003_1) 1965; 1769 Orsini F. (jo9911286b00010/jo9911286b00010_1) 1989; 367 Sutherland J. K. (jo9911286b00002/jo9911286b00002_1) 1967; 25 Meng D. F. (jo9911286b00004/jo9911286b00004_6) 1999; 38 Nicolaou K. C. (jo9911286b00005/jo9911286b00005_2) 1999; 38 Dabrah T. T. (jo9911286b00001/jo9911286b00001_2) 1997; 119 Agnelli F. (jo9911286b00010/jo9911286b00010_2) 1998; 39 Kwon O. Y. (jo9911286b00004/jo9911286b00004_5) 1998; 37 Bloomer J. L. (jo9911286b00006/jo9911286b00006_1) 1968; 588 Nicolaou K. C. (jo9911286b00005/jo9911286b00005_1) 1997; 36 Huff R. K. (jo9911286b00006/jo9911286b00006_2) 1972; 20 Clive D. L. J. (jo9911286b00004/jo9911286b00004_4) 1999; 40 Bio M. M. (jo9911286b00004/jo9911286b00004_2) 1999; 121 Nicolaou K. C. (jo9911286b00005/jo9911286b00005_5) 1999; 38 Dabrah T. T. (jo9911286b00001/jo9911286b00001_1) 1997; 50 Barton D. H. R. (jo9911286b00003/jo9911286b00003_2) 1965; 1772 Baldwin J. E. (jo9911286b00007/jo9911286b00007_1) 1999; 55 Baldwin J. E. (jo9911286b00002/jo9911286b00002_2) 1962; 18 Barton D. H. R. (jo9911286b00003/jo9911286b00003_3) 1965; 1779 Sgarbi P. W. M. (jo9911286b00004/jo9911286b00004_7) 1997; 2157 Suzuki A. (jo9911286b00009/jo9911286b00009_1) 1982; 15 jo9911286b00008/jo9911286b00008_1 Moppett C. E. (jo9911286b00006/jo9911286b00006_3) 1966; 772 Chen C. (jo9911286b00004/jo9911286b00004_3) 1998; 120 Nicolaou K. C. (jo9911286b00005/jo9911286b00005_4) 1999; 38 Huff R. K. (jo9911286b00006/jo9911286b00006_4) 1968; 1192 Waizumi N. (jo9911286b00004/jo9911286b00004_8) 1998; 39 Nicolaou K. C. (jo9911286b00005/jo9911286b00005_3) 1997; 36 |
| References_xml | – volume: 39 start-page: 8807 year: 1998 ident: WOS:000076995300016 article-title: Synthesis of arylacetates by the palladium-catalyzed cross-coupling of aryl bromides and copper(II) enolates publication-title: TETRAHEDRON LETTERS contributor: fullname: Agnelli, F – volume: 15 start-page: 178 year: 1982 ident: WOS:A1982NX81200004 article-title: ORGANOBORATES IN NEW SYNTHETIC REACTIONS publication-title: ACCOUNTS OF CHEMICAL RESEARCH contributor: fullname: SUZUKI, A – start-page: 2157 year: 1997 ident: WOS:A1997YG75800013 article-title: Synthesis of the carbobicyclic substructure of CP-225,917 and CP-263,114 publication-title: CHEMICAL COMMUNICATIONS contributor: fullname: Sgarbi, PWM – start-page: 1192 year: 1968 ident: WOS:A1968B907500037 article-title: A NOVEL SYNTHESIS OF A 9-MEMBERED RING publication-title: CHEMICAL COMMUNICATIONS contributor: fullname: HUFF, RK – volume: 36 start-page: 2821 year: 1997 ident: WOS:000071469300038 article-title: A novel approach to the CP-225,917 and CP-263,114 core publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Nicolaou, KC – volume: 38 start-page: 1676 year: 1999 ident: WOS:000080694400034 article-title: Total synthesis of the CP molecules CP-225,917 and CP-263,114 - Part 2: Evolution of the final strategy publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Nicolaou, KC – volume: 40 start-page: 4605 year: 1999 ident: WOS:000080742600002 article-title: Synthesis of tricyclic bridgehead olefins related to the core structure of CP-225,917 and CP-263,114 - solvent, strain, and substitution effects on siloxy-Cope rearrangements publication-title: TETRAHEDRON LETTERS contributor: fullname: Clive, DLJ – volume: 18 start-page: 345 year: 1962 ident: MEDLINE:13864341 article-title: The constitutions of glauconic, glaucanic and byssochlamic acids. publication-title: Experientia contributor: fullname: BALDWIN, J E – volume: 38 start-page: 549 year: 1999 ident: WOS:000078704200029 article-title: A novel route to the fused maleic anhydride moiety of CP molecules publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Nicolaou, KC – volume: 119 start-page: 1594 year: 1997 ident: WOS:A1997WJ09700011 article-title: CP-225,917 and CP-263,114: Novel ras farnesylation inhibitors from an unidentified fungus .2. Structure elucidation publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Dabrah, TT – start-page: 1779 year: 1996 ident: WOS:000084905400010.7 publication-title: J CHEM SOC contributor: fullname: BARTON DH – start-page: 1769 year: 1965 ident: WOS:A19656270700032 article-title: NONADRIDES .I. INTRODUCTION AND GENERAL SURVEY publication-title: JOURNAL OF THE CHEMICAL SOCIETY contributor: fullname: BARTON, DHR – volume: 38 start-page: 1669 year: 1999 ident: WOS:000080694400033 article-title: Total synthesis of the CP molecules CP-263,114 and CP-225,917 - Part 1: Synthesis of key intermediates and intelligence gathering publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Nicolaou, KC – volume: 37 start-page: 1880 year: 1998 ident: WOS:000075330000021 article-title: A stereospecific geminal alkylation scheme en route to CP-225,917 and CP-263,114 publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Kwon, OY – volume: 38 start-page: 1485 year: 1999 ident: WOS:000080448400036 article-title: Stereospecific sulfur-mediated cleavage of a spirocyclobutanone: Synthesis of a fully functional precursor to the CP compounds publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Meng, DF – volume: 50 start-page: 1 year: 1997 ident: WOS:A1997WE84800001 article-title: CP-225,917 and CP-263,114, novel Ras farnesylation inhibitors from an unidentified fungus .1. Taxonomy, fermentation, isolation, and biochemical properties publication-title: JOURNAL OF ANTIBIOTICS contributor: fullname: Dabrah, TT – start-page: 772 year: 1966 ident: WOS:A19668460800007 article-title: BIOSYNTHESIS OF GLAUCONIC ACID - C9 PRECURSORS publication-title: CHEMICAL COMMUNICATIONS contributor: fullname: MOPPETT, CE – volume: 55 start-page: 7363 year: 1999 ident: WOS:000080579800021 article-title: Reinvestigation of the dimerisation process forming isoglaucanic acid publication-title: TETRAHEDRON contributor: fullname: Baldwin, JE – start-page: 1772 year: 1965 ident: WOS:A19656270700033 article-title: NONADRIDES .2. CONSTITUTIONS OF GLAUCONIC AND GLAUCANIC ACIDS publication-title: JOURNAL OF THE CHEMICAL SOCIETY contributor: fullname: BARTON, DHR – volume: 20 start-page: 2584 year: 1972 ident: WOS:000084905400010.16 publication-title: J CHEM SOC P1 contributor: fullname: HUFF RK – start-page: 32 year: 1997 ident: WOS:000084905400010.14 publication-title: ACETATE PATHWAY FATT contributor: fullname: DEWICK PM – start-page: 588 year: 1968 ident: WOS:A1968A718600025 article-title: NONADRIDES .V. BISOYNTHESIS OF GLAUCONIC ACID publication-title: JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC contributor: fullname: BLOOMER, JL – volume: 367 start-page: 375 year: 1989 ident: WOS:A1989U779900012 article-title: INFLUENCE OF THE CATALYST ON THE PD(0)-MEDIATED REACTIONS OF BRZNCH(CH3)COO-TERT-BU WITH VINYL AND ARYL TRIFLATES publication-title: JOURNAL OF ORGANOMETALLIC CHEMISTRY contributor: fullname: ORSINI, F – volume: 37 start-page: 1877 year: 1998 ident: WOS:000075330000020 article-title: Total syntheses of CP-225,917 and CP-263,114: Creation of a matrix structure by sequential aldol condensation and intramolecular Heck ring closure publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Kwon, OY – volume: 120 start-page: 10784 year: 1998 ident: WOS:000076666800038 article-title: Stereospecific synthesis of the CP-263,114 core structure publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Chen, C – volume: 121 start-page: 890 year: 1999 ident: WOS:000078471800049 article-title: An approach to the synthesis of CP-263,114: A remarkably facile silyloxy-cope rearrangement publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Bio, MM – start-page: 552 year: 1998 ident: WOS:000074207500034 article-title: Synthesis of the bicyclo[4.3.1]decenone core of CP-225,917 and CP-263,114 publication-title: SYNLETT contributor: fullname: Armstrong, A – volume: 25 start-page: 131 year: 1967 ident: WOS:A1967A249500004 article-title: NONADRIDES publication-title: FORTSCHRITTE DER CHEMIE ORGANISCHER NATURSTOFFE contributor: fullname: SUTHERLAND, JK – volume: 39 start-page: 6015 year: 1998 ident: WOS:000075041200038 article-title: Synthetic studies on CP-225,917 and CP-263,114 publication-title: TETRAHEDRON LETTERS contributor: fullname: Waizumi, N – volume: 36 start-page: 1194 year: 1997 ident: WOS:A1997XJ96000014 article-title: Synthesis of the bicyclic core of CP-225,917 and CP-263,114 by an intramolecular Diels-Alder reaction publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH contributor: fullname: Nicolaou, KC – volume: 50 start-page: 7 year: 1997 ident: jo9911286b00001/jo9911286b00001_1 publication-title: J. Antibiot. doi: 10.7164/antibiotics.50.1 contributor: fullname: Dabrah T. T. – volume: 39 start-page: 6018 year: 1998 ident: jo9911286b00004/jo9911286b00004_8 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(98)01236-2 contributor: fullname: Waizumi N. – volume: 367 start-page: 382 year: 1989 ident: jo9911286b00010/jo9911286b00010_1 publication-title: J. Organomet. Chem. doi: 10.1016/0022-328X(89)87059-7 contributor: fullname: Orsini F. – volume: 1192 start-page: 1193 year: 1968 ident: jo9911286b00006/jo9911286b00006_4 publication-title: Chem. Commun. contributor: fullname: Huff R. K. – volume: 55 start-page: 7374 year: 1999 ident: jo9911286b00007/jo9911286b00007_1 publication-title: J. Tetrahedron doi: 10.1016/S0040-4020(99)00360-9 contributor: fullname: Baldwin J. E. – ident: jo9911286b00008/jo9911286b00008_1 – volume: 119 start-page: 1598 year: 1997 ident: jo9911286b00001/jo9911286b00001_2 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja961000v contributor: fullname: Dabrah T. T. – volume: 20 start-page: 2590 year: 1972 ident: jo9911286b00006/jo9911286b00006_2 publication-title: J. Chem. Soc., Perkin Trans. 1 contributor: fullname: Huff R. K. – volume: 38 start-page: 1678 year: 1999 ident: jo9911286b00005/jo9911286b00005_4 publication-title: Angew. Chem., Int. Ed. Engl. contributor: fullname: Nicolaou K. C. – volume: 38 start-page: 552 year: 1999 ident: jo9911286b00005/jo9911286b00005_5 publication-title: Angew. Chem., Int. Ed. Engl. doi: 10.1002/(SICI)1521-3773(19990215)38:4<552::AID-ANIE552>3.0.CO;2-B contributor: fullname: Nicolaou K. C. – volume: 1779 start-page: 1786 year: 1965 ident: jo9911286b00003/jo9911286b00003_3 publication-title: J. Chem. Soc. contributor: fullname: Barton D. H. R. – volume: 38 start-page: 1488 year: 1999 ident: jo9911286b00004/jo9911286b00004_6 publication-title: J. Angew. Chem., Int. Ed. Engl. contributor: fullname: Meng D. F. – volume: 37 start-page: 1882 year: 1998 ident: jo9911286b00004/jo9911286b00004_5 publication-title: J. Angew. Chem., Int. Ed. Engl. doi: 10.1002/(SICI)1521-3773(19980803)37:13/14<1882::AID-ANIE1882>3.0.CO;2-U contributor: fullname: Kwon O. Y. – volume: 1772 start-page: 1778 year: 1965 ident: jo9911286b00003/jo9911286b00003_2 publication-title: J. Chem. Soc. contributor: fullname: Barton D. H. R. – volume: 39 start-page: 8810 year: 1998 ident: jo9911286b00010/jo9911286b00010_2 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(98)01978-9 contributor: fullname: Agnelli F. – volume: 40 start-page: 4609 year: 1999 ident: jo9911286b00004/jo9911286b00004_4 publication-title: Tetrahedron Lett. contributor: fullname: Clive D. L. J. – volume: 18 start-page: 388 year: 1962 ident: jo9911286b00002/jo9911286b00002_2 publication-title: Experentia doi: 10.1007/BF02172243 contributor: fullname: Baldwin J. E. – volume: 120 start-page: 10785 year: 1998 ident: jo9911286b00004/jo9911286b00004_3 publication-title: J. Am. Chem. Soc. contributor: fullname: Chen C. – volume: 2157 start-page: 2158 year: 1997 ident: jo9911286b00004/jo9911286b00004_7 publication-title: J. Chem. Soc., Chem. Commun. contributor: fullname: Sgarbi P. W. M. – volume: 25 start-page: 149 year: 1967 ident: jo9911286b00002/jo9911286b00002_1 publication-title: Fortschr. Chem. Org. Naturst. contributor: fullname: Sutherland J. K. – volume: 15 start-page: 84 year: 1982 ident: jo9911286b00009/jo9911286b00009_1 publication-title: Acc. Chem. Res. doi: 10.1021/ar00078a003 contributor: fullname: Suzuki A. – volume: 36 start-page: 2823 year: 1997 ident: jo9911286b00005/jo9911286b00005_1 publication-title: Angew. Chem., Int. Ed. Engl. doi: 10.1002/anie.199728231 contributor: fullname: Nicolaou K. C. – volume: 36 start-page: 1196 year: 1997 ident: jo9911286b00005/jo9911286b00005_3 publication-title: Angew. Chem., Int. Ed. Engl. doi: 10.1002/anie.199711961 contributor: fullname: Nicolaou K. C. – volume: 1769 start-page: 1771 year: 1965 ident: jo9911286b00003/jo9911286b00003_1 publication-title: J. Chem. Soc. contributor: fullname: Barton D. H. R. – volume: 588 start-page: 591 year: 1968 ident: jo9911286b00006/jo9911286b00006_1 publication-title: J. Chem. Soc. C contributor: fullname: Bloomer J. L. – volume: 121 start-page: 891 year: 1999 ident: jo9911286b00004/jo9911286b00004_2 publication-title: J. Am. Chem. Soc. contributor: fullname: Bio M. M. – volume: 38 start-page: 1675 year: 1999 ident: jo9911286b00005/jo9911286b00005_2 publication-title: Angew. Chem., Int. Ed. Engl. contributor: fullname: Nicolaou K. C. – volume: 772 start-page: 773 year: 1966 ident: jo9911286b00006/jo9911286b00006_3 publication-title: Chem. Commun. contributor: fullname: Moppett C. E. – volume: 552 start-page: 553 year: 1998 ident: jo9911286b00004/jo9911286b00004_1 publication-title: Synlett contributor: fullname: Armstrong A. |
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| Snippet | A biosynthesis of the structurally complex nonadride CP-225,917 (1) is outlined. A key step in this proposal is the dimerization of a C16 anhydride derived... A biosynthesis of the structurally complex nonadride CP-225,917 (1) is outlined. A key step in this proposal is the dimerization of a C-16 anhydride derived... A biosynthesis of the structurally complex nonadride CP-225,917 (1) is outlined. A key step in this proposal is the dimerization of a C(16) anhydride derived... |
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| SubjectTerms | Chemistry Chemistry, Organic Enzyme Inhibitors - chemistry Enzyme Inhibitors - metabolism Farnesyl-Diphosphate Farnesyltransferase - antagonists & inhibitors Maleic Anhydrides - chemistry Maleic Anhydrides - metabolism Molecular Mimicry Molecular Structure Physical Sciences Science & Technology Spectrum Analysis |
| Title | Investigations into a Biomimetic Approach toward CP-225,917 and CP-263,114 |
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