Kedarcidin Chromophore: Synthesis of Its Proposed Structure and Evidence for a Stereochemical Revision
A convergent, enantioselective synthesis of the proposed structure of kedarcidin chromophore (1) is described. The route is 24 steps in the longest linear sequence (beginning with the commercial reagent 2,3-O-isopropylidene-d-erythronolactone) with an average yield of 75% per step (overall yield: 0...
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| Published in | Journal of the American Chemical Society Vol. 129; no. 17; pp. 5381 - 5383 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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WASHINGTON
American Chemical Society
02.05.2007
Amer Chemical Soc |
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| Abstract | A convergent, enantioselective synthesis of the proposed structure of kedarcidin chromophore (1) is described. The route is 24 steps in the longest linear sequence (beginning with the commercial reagent 2,3-O-isopropylidene-d-erythronolactone) with an average yield of 75% per step (overall yield: 0.1%). Our 1H NMR data for 1 do not coincide with the data reported for kedarcidin chromophore. We have re-analyzed the original data and here propose a stereochemical revision at position C10, the site of attachment of the l-mycarose carbohydrate residue to the chromophore core (structure 2). |
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| AbstractList | A convergent, enantioselective synthesis of the proposed structure of kedarcidin chromophore (
1
) is described. The route is 24 steps in the longest linear sequence (beginning with the commercial reagent 2,3-
O
-isopropylidene-
d
-erythronolactone) with an average yield of 75% per step (overall yield: 0.1%). Our
1
H NMR data for
1
do not coincide with the data reported for kedarcidin chromophore. We have re-analyzed the original data and here propose a stereochemical revision at position C10, the site of attachment of the
l
-mycarose carbohydrate residue to the chromophore core (structure
2
). A convergent, enantioselective synthesis of the proposed structure of kedarcidin chromophore (1) is described. The route is 24 steps in the longest linear sequence (beginning with the commercial reagent 2,3-O-isopropylidene-d-erythronolactone) with an average yield of 75% per step (overall yield: 0.1%). Our 1H NMR data for 1 do not coincide with the data reported for kedarcidin chromophore. We have re-analyzed the original data and here propose a stereochemical revision at position C10, the site of attachment of the l-mycarose carbohydrate residue to the chromophore core (structure 2). A convergent, enantioselective synthesis of the proposed structure of kedarcidin chromophore (1) is described. The route is 24 steps in the longest linear sequence (beginning with the commercial reagent 2,3-O-isopropylidene-D-erythronolactone) with an average yield of 75% per step (overall yield: 0.1%). Our H-1 NMR data for 1 do not coincide with the data reported for kedarcidin chromophore. We have re-analyzed the original data and here propose a stereochemical revision at position C10, the site of attachment of the L-mycarose carbohydrate residue to the chromophore core (structure 2>). |
| Author | Hogan, Philip C Myers, Andrew G Anderson, Alan J Ren, Feng |
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| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/17417855$$D View this record in MEDLINE/PubMed |
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| Cites_doi | 10.1021/ja020152p 10.1016/j.tet.2004.01.045 10.1016/j.tet.2004.06.071 10.1021/ol030017x 10.1016/S0040-4039(97)00844-7 10.1016/S0040-4039(00)60018-7 10.1351/pac200375010039 10.1016/S0040-4039(01)80327-0 10.1021/ja973231n 10.1016/0040-4039(96)01036-2 10.1016/S0040-4020(02)00287-9 10.1021/jo00290a015 10.1016/S0040-4039(00)81385-4 10.1039/jr9590000889 10.1002/1521-3773(20000804)39:15<2732::AID-ANIE2732>3.0.CO;2-9 10.1016/S0040-4039(02)01819-1 10.1246/cl.2002.286 10.1002/1521-3773(20020315)41:6<1062::AID-ANIE1062>3.0.CO;2-8 10.1016/S0040-4039(01)86696-X 10.1021/jo00837a701 10.1021/ja00071a062 10.1002/1521-3773(20010302)40:5<946::AID-ANIE946>3.0.CO;2-G 10.1021/ja00046a071 |
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| Keywords | ENANTIOSELECTIVE SYNTHESIS 2-METHYL-6-NITROBENZOIC ANHYDRIDE ACIDS ESTERS SELECTIVE SYNTHESIS AGLYCON STRUCTURE ELUCIDATION SUGAR |
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| References | LEET, JE (WOS:A1993LX75200062) 1993; 115 Sato, I (WOS:A1996UY35500031) 1996; 37 Ellman, JA (WOS:000181536400005) 2003; 75 Kawata, S (WOS:A1997YK70800044) 1997; 119 ROSSITER BE (WOS:000245946400041.19) 1979; 20 LEET, JE (WOS:A1992JT09100018) 1992; 33 HOGAN PC (WOS:000245946400041.5) 2004 REN F (WOS:000245946400041.17) SAKAITANI, M (WOS:A1990CM52200015) 1990; 55 Myers, AG (WOS:000174450300036) 2002; 41 Myers, AG (WOS:000175227600024) 2002; 124 EGLINTON, G (WOS:A1959WK68400008) 1959 RICHARDS.WH (WOS:A1970I011100002) 1970; 35 Shi, JC (WOS:000183129000005) 2003; 5 Zhou, P (WOS:000223609800001) 2004; 60 Shiina, I (WOS:000174591300011) 2002 PEREZ, M (WOS:A1989R911300020) 1989; 30 LEET, JE (WOS:A1992JP51200071) 1992; 114 Myers, AG (WOS:A1997XF71400010) 1997; 38 Shiina, I (WOS:000178397400019) 2002; 43 Lear, MJ (WOS:000167323100026) 2001; 40 KESSLER, H (WOS:A1983PY03600015) 1983; 24 Bickley, JF (WOS:000220035400013) 2004; 60 Myers, AG (WOS:000088702200020) 2000; 39 Comin, MJ (WOS:000175933700002) 2002; 58 For (ja071205bb00010/ja071205bb00010_1) 2003; 5 Richardson W. H. (ja071205bb00016/ja071205bb00016_1) 1970; 35 Leet J. E. (ja071205bb00001/ja071205bb00001_1) 1992; 114 Kessler H. (ja071205bb00005/ja071205bb00005_1) 1983; 24 Shiina I. (ja071205bb00011/ja071205bb00011_1) 2002; 43 Kawata S. (ja071205bb00002/ja071205bb00002_1) 1997; 119 Shiina I. (ja071205bb00006/ja071205bb00006_1) 2002 Ellman J. A. (ja071205bb00004/ja071205bb00004_2) 2003; 75 Sato I. (ja071205bb00012/ja071205bb00012_1) 1996; 37 Perez M. (ja071205bb00020/ja071205bb00020_3) 1989; 30 Myers A. G. (ja071205bb00003/ja071205bb00003_1) 2000; 39 Leet J. E. (ja071205bb00001/ja071205bb00001_2) 1993; 115 Myers A. G. (ja071205bb00003/ja071205bb00003_3) 2002; 124 Zhou P. (ja071205bb00004/ja071205bb00004_1) 2004; 60 Rossiter B. E. (ja071205bb00015/ja071205bb00015_1) 1979; 20 Comin M. J. (ja071205bb00020/ja071205bb00020_1) 2002; 58 Bickley J. F. (ja071205bb00020/ja071205bb00020_2) 2004; 60 Ren F. (ja071205bb00009/ja071205bb00009_1) Eglinton G. (ja071205bb00013/ja071205bb00013_1) 1959 Myers A. G. (ja071205bb00008/ja071205bb00008_1) 1997; 38 Hogan P. C. Ph.D. (ja071205bb00008/ja071205bb00008_2) 2004 Leet J. E. (ja071205bb00019/ja071205bb00019_1) 1992; 33 Myers A. G. (ja071205bb00003/ja071205bb00003_2) 2002; 41 Lear M. J. (ja071205bb00018/ja071205bb00018_1) 2001; 40 Sakaitani M. (ja071205bb00007/ja071205bb00007_1) 1990; 55 |
| References_xml | – volume: 124 start-page: 4583 year: 2002 ident: WOS:000175227600024 article-title: Evidence for facile atropisomerism and simple (non-nucleophilic) biradical-forming cycloaromatization within kedarcidin chromophore aglycon publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja020152p contributor: fullname: Myers, AG – volume: 38 start-page: 4363 year: 1997 ident: WOS:A1997XF71400010 article-title: Synthesis of the naphthoic acid component of kedarcidin chromophore by routes employing photochemical and thermal electrocyclic ring closure reactions. publication-title: TETRAHEDRON LETTERS contributor: fullname: Myers, AG – volume: 58 start-page: 3129 year: 2002 ident: WOS:000175933700002 article-title: Enantioselective synthesis of (+)-neplanocin F publication-title: TETRAHEDRON contributor: fullname: Comin, MJ – volume: 55 start-page: 870 year: 1990 ident: WOS:A1990CM52200015 article-title: SYNTHESES AND REACTIONS OF SILYL CARBAMATES .1. CHEMOSELECTIVE TRANSFORMATION OF AMINO PROTECTING GROUPS VIA TERT-BUTYLDIMETHYLSILYL CARBAMATES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: SAKAITANI, M – volume: 60 start-page: 2569 year: 2004 ident: WOS:000220035400013 article-title: Synthesis and revision of the stereochemistry of a cyclopentenone natural product isolated from ascomycete strain A23-98 publication-title: TETRAHEDRON doi: 10.1016/j.tet.2004.01.045 contributor: fullname: Bickley, JF – volume: 40 start-page: 946 year: 2001 ident: WOS:000167323100026 article-title: A direct and efficient alpha-selective glycosylation protocol for the kedarcidin sugar, L-mycarose: AgPF6 as a remarkable activator of 2-deoxythioglycosides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Lear, MJ – volume: 30 start-page: 75 year: 1989 ident: WOS:A1989R911300020 article-title: SELENIUM-MEDIATED GLYCOSIDATIONS - A SELECTIVE SYNTHESIS OF BETA-2-DEOXYGLYCOSIDES publication-title: TETRAHEDRON LETTERS contributor: fullname: PEREZ, M – volume: 39 start-page: 2732 year: 2000 ident: WOS:000088702200020 article-title: Synthesis of the kedarcidin core structure by a transannular cyclization pathway publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Myers, AG – start-page: 889 year: 1959 ident: WOS:A1959WK68400008 article-title: MACROCYCLIC ACETYLENIC COMPOUNDS .1. CYCLOTETRADECA-1,3-DIYNE AND RELATED COMPOUNDS publication-title: JOURNAL OF THE CHEMICAL SOCIETY contributor: fullname: EGLINTON, G – year: 2004 ident: WOS:000245946400041.5 publication-title: THESIS HARVARD U CAM contributor: fullname: HOGAN PC – volume: 37 start-page: 5135 year: 1996 ident: WOS:A1996UY35500031 article-title: Efficient synthesis of a carbocyclic core moiety with the stereochemistry of the C-1027 chromophore publication-title: TETRAHEDRON LETTERS contributor: fullname: Sato, I – volume: 114 start-page: 7946 year: 1992 ident: WOS:A1992JP51200071 article-title: KEDARCIDIN, A NEW CHROMOPROTEIN ANTITUMOR ANTIBIOTIC - STRUCTURE ELUCIDATION OF KEDARCIDIN CHROMOPHORE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: LEET, JE – volume: 33 start-page: 6107 year: 1992 ident: WOS:A1992JT09100018 article-title: KEDARCIDIN CHROMOPHORE - STRUCTURE ELUCIDATION OF THE AMINO SUGAR KEDAROSAMINE publication-title: TETRAHEDRON LETTERS contributor: fullname: LEET, JE – volume: 20 start-page: 4733 year: 1979 ident: WOS:000245946400041.19 publication-title: TETRAHEDRON LETT contributor: fullname: ROSSITER BE – volume: 60 start-page: 8003 year: 2004 ident: WOS:000223609800001 article-title: Recent advances in asymmetric reactions using sulfinimines (N-sulfinyl imines) publication-title: TETRAHEDRON doi: 10.1016/j.tet.2004.06.071 contributor: fullname: Zhou, P – volume: 24 start-page: 281 year: 1983 ident: WOS:A1983PY03600015 article-title: 9-FLUORENYLMETHYL ESTERS AS CARBOXYL PROTECTING GROUP publication-title: TETRAHEDRON LETTERS contributor: fullname: KESSLER, H – start-page: 286 year: 2002 ident: WOS:000174591300011 article-title: A new condensation reaction for the synthesis of carboxylic esters from nearly equimolar amounts of carboxylic acids and alcohols using 2-methyl-6-nitrobenzoic anhydride publication-title: CHEMISTRY LETTERS contributor: fullname: Shiina, I – volume: 43 start-page: 7535 year: 2002 ident: WOS:000178397400019 article-title: A novel and efficient macrolactonization of omega-hydroxycarboxylic acids using 2-methyl-6-nitrobenzoic anhydride (MNBA) publication-title: TETRAHEDRON LETTERS contributor: fullname: Shiina, I – volume: 35 start-page: 4012 year: 1970 ident: WOS:A1970I011100002 article-title: ACIDITIES OF TERTIARY ALKYL HYDROPEROXIDES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: RICHARDS.WH – volume: 115 start-page: 8432 year: 1993 ident: WOS:A1993LX75200062 article-title: CHEMISTRY AND STRUCTURE ELUCIDATION OF THE KEDARCIDIN CHROMOPHORE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: LEET, JE – volume: 75 start-page: 39 year: 2003 ident: WOS:000181536400005 article-title: Applications of tert-butanesulfinamide in the asymmetric synthesis of amines publication-title: PURE AND APPLIED CHEMISTRY contributor: fullname: Ellman, JA – volume: 119 start-page: 12012 year: 1997 ident: WOS:A1997YK70800044 article-title: Synthetic study of kedarcidin chromophore: Revised structure publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: Kawata, S – volume: 41 start-page: 1062 year: 2002 ident: WOS:000174450300036 article-title: Enantioselective synthesis of kedarcidin chromophore aglycon in differentially protected form publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION contributor: fullname: Myers, AG – ident: WOS:000245946400041.17 publication-title: UNPUB ORG LETT contributor: fullname: REN F – volume: 5 start-page: 1825 year: 2003 ident: WOS:000183129000005 article-title: Highly selective synthesis of (E)-3-methyl-1-trialkylsilyl-3-en-1-ynes via trans-selective alkynylation catalyzed by Cl2Pd(DPEphos) and stereospecific methylation with methylzincs catalyzed by Pd((Bu3P)-Bu-t)(2) publication-title: ORGANIC LETTERS doi: 10.1021/ol030017x contributor: fullname: Shi, JC – volume: 38 start-page: 4363 year: 1997 ident: ja071205bb00008/ja071205bb00008_1 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(97)00844-7 contributor: fullname: Myers A. G. – volume: 60 start-page: 2569 year: 2004 ident: ja071205bb00020/ja071205bb00020_2 publication-title: J. Tetrahedron doi: 10.1016/j.tet.2004.01.045 contributor: fullname: Bickley J. F. – volume: 33 start-page: 6107 year: 1992 ident: ja071205bb00019/ja071205bb00019_1 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)60018-7 contributor: fullname: Leet J. E. – volume: 75 start-page: 39 year: 2003 ident: ja071205bb00004/ja071205bb00004_2 publication-title: Pure Appl. Chem. doi: 10.1351/pac200375010039 contributor: fullname: Ellman J. A. – volume: 30 start-page: 75 year: 1989 ident: ja071205bb00020/ja071205bb00020_3 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(01)80327-0 contributor: fullname: Perez M. – volume: 119 start-page: 12012 year: 1997 ident: ja071205bb00002/ja071205bb00002_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja973231n contributor: fullname: Kawata S. – volume: 37 start-page: 5135 year: 1996 ident: ja071205bb00012/ja071205bb00012_1 publication-title: Tetrahedron Lett. doi: 10.1016/0040-4039(96)01036-2 contributor: fullname: Sato I. – volume: 5 start-page: 1825 year: 2003 ident: ja071205bb00010/ja071205bb00010_1 publication-title: Org. Lett. doi: 10.1021/ol030017x contributor: fullname: For – volume: 58 start-page: 3129 year: 2002 ident: ja071205bb00020/ja071205bb00020_1 publication-title: Tetrahedron doi: 10.1016/S0040-4020(02)00287-9 contributor: fullname: Comin M. J. – volume: 55 start-page: 870 year: 1990 ident: ja071205bb00007/ja071205bb00007_1 publication-title: J. Org. Chem. doi: 10.1021/jo00290a015 contributor: fullname: Sakaitani M. – volume: 24 start-page: 281 year: 1983 ident: ja071205bb00005/ja071205bb00005_1 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)81385-4 contributor: fullname: Kessler H. – start-page: 889 year: 1959 ident: ja071205bb00013/ja071205bb00013_1 publication-title: J. Chem. Soc. doi: 10.1039/jr9590000889 contributor: fullname: Eglinton G. – volume-title: Harvard University year: 2004 ident: ja071205bb00008/ja071205bb00008_2 contributor: fullname: Hogan P. C. Ph.D. – volume: 39 start-page: 2732 year: 2000 ident: ja071205bb00003/ja071205bb00003_1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/1521-3773(20000804)39:15<2732::AID-ANIE2732>3.0.CO;2-9 contributor: fullname: Myers A. G. – volume: 43 start-page: 7535 year: 2002 ident: ja071205bb00011/ja071205bb00011_1 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(02)01819-1 contributor: fullname: Shiina I. – start-page: 286 year: 2002 ident: ja071205bb00006/ja071205bb00006_1 publication-title: Chem. Lett. doi: 10.1246/cl.2002.286 contributor: fullname: Shiina I. – ident: ja071205bb00009/ja071205bb00009_1 publication-title: Org. Lett. Submitted. contributor: fullname: Ren F. – volume: 41 start-page: 1062 year: 2002 ident: ja071205bb00003/ja071205bb00003_2 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/1521-3773(20020315)41:6<1062::AID-ANIE1062>3.0.CO;2-8 contributor: fullname: Myers A. G. – volume: 20 start-page: 4733 year: 1979 ident: ja071205bb00015/ja071205bb00015_1 publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(01)86696-X contributor: fullname: Rossiter B. E. – volume: 60 start-page: 8003 year: 2004 ident: ja071205bb00004/ja071205bb00004_1 publication-title: Tetrahedron doi: 10.1016/j.tet.2004.06.071 contributor: fullname: Zhou P. – volume: 35 start-page: 4012 year: 1970 ident: ja071205bb00016/ja071205bb00016_1 publication-title: J. Org. Chem. doi: 10.1021/jo00837a701 contributor: fullname: Richardson W. H. – volume: 115 start-page: 8432 year: 1993 ident: ja071205bb00001/ja071205bb00001_2 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00071a062 contributor: fullname: Leet J. E. – volume: 40 start-page: 946 year: 2001 ident: ja071205bb00018/ja071205bb00018_1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/1521-3773(20010302)40:5<946::AID-ANIE946>3.0.CO;2-G contributor: fullname: Lear M. J. – volume: 114 start-page: 7946 year: 1992 ident: ja071205bb00001/ja071205bb00001_1 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00046a071 contributor: fullname: Leet J. E. – volume: 124 start-page: 4583 year: 2002 ident: ja071205bb00003/ja071205bb00003_3 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja020152p contributor: fullname: Myers A. G. |
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| Snippet | A convergent, enantioselective synthesis of the proposed structure of kedarcidin chromophore (1) is described. The route is 24 steps in the longest linear... A convergent, enantioselective synthesis of the proposed structure of kedarcidin chromophore ( 1 ) is described. The route is 24 steps in the longest linear... |
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| SubjectTerms | Antibiotics, Antineoplastic - chemical synthesis Antibiotics, Antineoplastic - chemistry Aza Compounds - chemistry Chemistry Chemistry, Multidisciplinary Cycloparaffins - chemical synthesis Cycloparaffins - chemistry Enediynes - chemical synthesis Enediynes - chemistry Indicators and Reagents Magnetic Resonance Spectroscopy Mass Spectrometry Molecular Conformation Naphthalenes - chemical synthesis Naphthalenes - chemistry Physical Sciences Science & Technology Spectroscopy, Fourier Transform Infrared Stereoisomerism |
| Title | Kedarcidin Chromophore: Synthesis of Its Proposed Structure and Evidence for a Stereochemical Revision |
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