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In Silico Inspired Total Synthesis of (-)-Dolabriferol
被引:14
作者
:
Currie, Russell H.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Unilever Ctr Mol Sci Informat, Cambridge CB2 8PH, England
Univ Cambridge, Dept Chem, Unilever Ctr Mol Sci Informat, Cambridge CB2 8PH, England
Currie, Russell H.
[
1
]
Goodman, Jonathan M.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Dept Chem, Unilever Ctr Mol Sci Informat, Cambridge CB2 8PH, England
Univ Cambridge, Dept Chem, Unilever Ctr Mol Sci Informat, Cambridge CB2 8PH, England
Goodman, Jonathan M.
[
1
]
机构
:
[1]
Univ Cambridge, Dept Chem, Unilever Ctr Mol Sci Informat, Cambridge CB2 8PH, England
来源
:
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
|
2012年
/ 51卷
/ 19期
基金
:
英国工程与自然科学研究理事会;
关键词
:
aldol reaction;
asymmetric synthesis;
biomimetic synthesis;
natural products;
polyketides;
LACTATE-DERIVED KETONES;
ANTI-ALDOL REACTIONS;
PI-FACE SELECTIVITY;
ENANTIOSELECTIVE SYNTHESIS;
POLYPROPIONATE SYNTHESIS;
DOLABRIFEROL;
REDUCTION;
PROGRAM;
MOIETY;
ROBIA;
D O I
:
10.1002/anie.201109080
中图分类号
:
O6 [化学];
学科分类号
:
0703 ;
摘要
:
Going retro: The diazabicycloundecane-induced retro-Claisen rearrangement of a linear precursor serves as the key step to form the hindered ester of the polypropionate dolabriferol (1, see scheme, PMB=p-methoxybenzyl, PMP=p-methoxyphenyl, TES=triethylsilyl). The rearrangement is thought to mimic the biosynthetic formation of 1. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:4695 / 4697
页数:3
相关论文
共 21 条
[1]
Synthetic Studies on Siphonariid Polypropionates: Synthesis and Isomerization of the Caloundrin B Trioxaadamantane Ring System
Beye, Garrison E.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
Beye, Garrison E.
Goodman, Jonathan M.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Univ Chem Lab, Cambridge CB2 1EW, England
Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
Goodman, Jonathan M.
Ward, Dale E.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
Ward, Dale E.
[J].
ORGANIC LETTERS,
2009,
11
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: 1373
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1376
[2]
New non-contiguous polypropionates from marine molluscs: A comment on their natural product status
Brecknell, DJ
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0
引用数:
0
h-index:
0
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Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa
Brecknell, DJ
Collett, LA
论文数:
0
引用数:
0
h-index:
0
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Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa
Collett, LA
Davies-Coleman, MT
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0
h-index:
0
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Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa
Davies-Coleman, MT
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0
引用数:
0
h-index:
0
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Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa
Garson, MJ
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论文数:
0
引用数:
0
h-index:
0
机构:
Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa
Jones, DD
[J].
TETRAHEDRON,
2000,
56
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[3]
Chemoenzymatic enantioselective synthesis of the polypropionate acid moiety of dolabriferol
Chênevert, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada
Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada
Chênevert, R
Courchesne, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada
Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada
Courchesne, G
Caron, D
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada
Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada
Caron, D
[J].
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2003,
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[4]
Dolabriferol: A new polypropionate from the skin of the anaspidean Mollusc Dolabrifera dolabrifera
Ciavatta, ML
论文数:
0
引用数:
0
h-index:
0
机构:
CNR,IST CHIM MOL INTERESSE BIOL,I-80072 ARCO,ITALY
Ciavatta, ML
Gavagnin, M
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0
引用数:
0
h-index:
0
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CNR,IST CHIM MOL INTERESSE BIOL,I-80072 ARCO,ITALY
Gavagnin, M
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0
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0
h-index:
0
机构:
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0
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0
h-index:
0
机构:
CNR,IST CHIM MOL INTERESSE BIOL,I-80072 ARCO,ITALY
Cimino, G
Martinez, E
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0
引用数:
0
h-index:
0
机构:
CNR,IST CHIM MOL INTERESSE BIOL,I-80072 ARCO,ITALY
Martinez, E
Ortea, J
论文数:
0
引用数:
0
h-index:
0
机构:
CNR,IST CHIM MOL INTERESSE BIOL,I-80072 ARCO,ITALY
Ortea, J
Mattia, CA
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0
引用数:
0
h-index:
0
机构:
CNR,IST CHIM MOL INTERESSE BIOL,I-80072 ARCO,ITALY
Mattia, CA
[J].
TETRAHEDRON,
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52
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: 12831
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12838
[5]
Synthetic studies directed toward the total synthesis of dolabriferol
Dias, LC
论文数:
0
引用数:
0
h-index:
0
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Univ Estadual Campinas, UNICAMP, Inst Quim, BR-13084971 Campinas, SP, Brazil
Univ Estadual Campinas, UNICAMP, Inst Quim, BR-13084971 Campinas, SP, Brazil
Dias, LC
de Sousa, MA
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0
h-index:
0
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Univ Estadual Campinas, UNICAMP, Inst Quim, BR-13084971 Campinas, SP, Brazil
de Sousa, MA
[J].
TETRAHEDRON LETTERS,
2003,
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: 5625
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5628
[6]
DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE
EVANS, DA
论文数:
0
引用数:
0
h-index:
0
EVANS, DA
CHAPMAN, KT
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0
引用数:
0
h-index:
0
CHAPMAN, KT
CARREIRA, EM
论文数:
0
引用数:
0
h-index:
0
CARREIRA, EM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1988,
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: 3560
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[7]
DIASTEREOSELECTIVE ANTIALDOL REACTIONS OF CHIRAL ETHYL KETONES - ENANTIOSELECTIVE PROCESSES FOR THE SYNTHESIS OF POLYPROPIONATE NATURAL-PRODUCTS
EVANS, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge, MA
EVANS, DA
NG, HP
论文数:
0
引用数:
0
h-index:
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Department of Chemistry, Harvard University, Cambridge, MA
NG, HP
CLARK, JS
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0
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Department of Chemistry, Harvard University, Cambridge, MA
CLARK, JS
RIEGER, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge, MA
RIEGER, DL
[J].
TETRAHEDRON,
1992,
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[8]
DIASTEREOSELECTIVE ALDOL REACTIONS USING BETA-KETO IMIDE DERIVED ENOLATES - A VERSATILE APPROACH TO THE ASSEMBLAGE OF POLYPROPIONATE SYSTEMS
EVANS, DA
论文数:
0
引用数:
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h-index:
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Department of Chemistry, Harvard University, Cambridge, Massachusetts
EVANS, DA
CLARK, JS
论文数:
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引用数:
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Department of Chemistry, Harvard University, Cambridge, Massachusetts
CLARK, JS
METTERNICH, R
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引用数:
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h-index:
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Department of Chemistry, Harvard University, Cambridge, Massachusetts
METTERNICH, R
NOVACK, VJ
论文数:
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引用数:
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h-index:
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Department of Chemistry, Harvard University, Cambridge, Massachusetts
NOVACK, VJ
SHEPPARD, GS
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge, Massachusetts
SHEPPARD, GS
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1990,
112
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: 866
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868
[9]
Laclef S., 2010, ANGEW CHEM, V122, P8704
[10]
Total Synthesis and Determination of the Absolute Configuration of (-)-Dolabriferol
Laclef, Sylvain
论文数:
0
引用数:
0
h-index:
0
机构:
Swiss Fed Inst Technol EPFL, Lab Glycochim & Synth Asymetr, CH-1015 Lausanne, Switzerland
Swiss Fed Inst Technol EPFL, Lab Glycochim & Synth Asymetr, CH-1015 Lausanne, Switzerland
Laclef, Sylvain
Turks, Maris
论文数:
0
引用数:
0
h-index:
0
机构:
Riga Tech Univ, Fac Mat Sci & Appl Chem, LV-1658 Riga, Latvia
Swiss Fed Inst Technol EPFL, Lab Glycochim & Synth Asymetr, CH-1015 Lausanne, Switzerland
Turks, Maris
Vogel, Pierre
论文数:
0
引用数:
0
h-index:
0
机构:
Swiss Fed Inst Technol EPFL, Lab Glycochim & Synth Asymetr, CH-1015 Lausanne, Switzerland
Swiss Fed Inst Technol EPFL, Lab Glycochim & Synth Asymetr, CH-1015 Lausanne, Switzerland
Vogel, Pierre
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2010,
49
(45)
: 8525
-
8527
←
1
2
3
→
共 21 条
[1]
Synthetic Studies on Siphonariid Polypropionates: Synthesis and Isomerization of the Caloundrin B Trioxaadamantane Ring System
Beye, Garrison E.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
Beye, Garrison E.
Goodman, Jonathan M.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Cambridge, Univ Chem Lab, Cambridge CB2 1EW, England
Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
Goodman, Jonathan M.
Ward, Dale E.
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada
Ward, Dale E.
[J].
ORGANIC LETTERS,
2009,
11
(06)
: 1373
-
1376
[2]
New non-contiguous polypropionates from marine molluscs: A comment on their natural product status
Brecknell, DJ
论文数:
0
引用数:
0
h-index:
0
机构:
Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa
Brecknell, DJ
Collett, LA
论文数:
0
引用数:
0
h-index:
0
机构:
Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa
Collett, LA
Davies-Coleman, MT
论文数:
0
引用数:
0
h-index:
0
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Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa
Davies-Coleman, MT
Garson, MJ
论文数:
0
引用数:
0
h-index:
0
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Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa
Garson, MJ
Jones, DD
论文数:
0
引用数:
0
h-index:
0
机构:
Rhodes Univ, Dept Chem, ZA-6140 Grahamstown, South Africa
Jones, DD
[J].
TETRAHEDRON,
2000,
56
(16)
: 2497
-
2502
[3]
Chemoenzymatic enantioselective synthesis of the polypropionate acid moiety of dolabriferol
Chênevert, R
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada
Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada
Chênevert, R
Courchesne, G
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada
Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada
Courchesne, G
Caron, D
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada
Univ Laval, Fac Sci & Genie, Dept Chim, Quebec City, PQ G1K 7P4, Canada
Caron, D
[J].
TETRAHEDRON-ASYMMETRY,
2003,
14
(17)
: 2567
-
2571
[4]
Dolabriferol: A new polypropionate from the skin of the anaspidean Mollusc Dolabrifera dolabrifera
Ciavatta, ML
论文数:
0
引用数:
0
h-index:
0
机构:
CNR,IST CHIM MOL INTERESSE BIOL,I-80072 ARCO,ITALY
Ciavatta, ML
Gavagnin, M
论文数:
0
引用数:
0
h-index:
0
机构:
CNR,IST CHIM MOL INTERESSE BIOL,I-80072 ARCO,ITALY
Gavagnin, M
Puliti, R
论文数:
0
引用数:
0
h-index:
0
机构:
CNR,IST CHIM MOL INTERESSE BIOL,I-80072 ARCO,ITALY
Puliti, R
Cimino, G
论文数:
0
引用数:
0
h-index:
0
机构:
CNR,IST CHIM MOL INTERESSE BIOL,I-80072 ARCO,ITALY
Cimino, G
Martinez, E
论文数:
0
引用数:
0
h-index:
0
机构:
CNR,IST CHIM MOL INTERESSE BIOL,I-80072 ARCO,ITALY
Martinez, E
Ortea, J
论文数:
0
引用数:
0
h-index:
0
机构:
CNR,IST CHIM MOL INTERESSE BIOL,I-80072 ARCO,ITALY
Ortea, J
Mattia, CA
论文数:
0
引用数:
0
h-index:
0
机构:
CNR,IST CHIM MOL INTERESSE BIOL,I-80072 ARCO,ITALY
Mattia, CA
[J].
TETRAHEDRON,
1996,
52
(39)
: 12831
-
12838
[5]
Synthetic studies directed toward the total synthesis of dolabriferol
Dias, LC
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Estadual Campinas, UNICAMP, Inst Quim, BR-13084971 Campinas, SP, Brazil
Univ Estadual Campinas, UNICAMP, Inst Quim, BR-13084971 Campinas, SP, Brazil
Dias, LC
de Sousa, MA
论文数:
0
引用数:
0
h-index:
0
机构:
Univ Estadual Campinas, UNICAMP, Inst Quim, BR-13084971 Campinas, SP, Brazil
Univ Estadual Campinas, UNICAMP, Inst Quim, BR-13084971 Campinas, SP, Brazil
de Sousa, MA
[J].
TETRAHEDRON LETTERS,
2003,
44
(30)
: 5625
-
5628
[6]
DIRECTED REDUCTION OF BETA-HYDROXY KETONES EMPLOYING TETRAMETHYLAMMONIUM TRIACETOXYBOROHYDRIDE
EVANS, DA
论文数:
0
引用数:
0
h-index:
0
EVANS, DA
CHAPMAN, KT
论文数:
0
引用数:
0
h-index:
0
CHAPMAN, KT
CARREIRA, EM
论文数:
0
引用数:
0
h-index:
0
CARREIRA, EM
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1988,
110
(11)
: 3560
-
3578
[7]
DIASTEREOSELECTIVE ANTIALDOL REACTIONS OF CHIRAL ETHYL KETONES - ENANTIOSELECTIVE PROCESSES FOR THE SYNTHESIS OF POLYPROPIONATE NATURAL-PRODUCTS
EVANS, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge, MA
EVANS, DA
NG, HP
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge, MA
NG, HP
CLARK, JS
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge, MA
CLARK, JS
RIEGER, DL
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge, MA
RIEGER, DL
[J].
TETRAHEDRON,
1992,
48
(11)
: 2127
-
2142
[8]
DIASTEREOSELECTIVE ALDOL REACTIONS USING BETA-KETO IMIDE DERIVED ENOLATES - A VERSATILE APPROACH TO THE ASSEMBLAGE OF POLYPROPIONATE SYSTEMS
EVANS, DA
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge, Massachusetts
EVANS, DA
CLARK, JS
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge, Massachusetts
CLARK, JS
METTERNICH, R
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge, Massachusetts
METTERNICH, R
NOVACK, VJ
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge, Massachusetts
NOVACK, VJ
SHEPPARD, GS
论文数:
0
引用数:
0
h-index:
0
机构:
Department of Chemistry, Harvard University, Cambridge, Massachusetts
SHEPPARD, GS
[J].
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,
1990,
112
(02)
: 866
-
868
[9]
Laclef S., 2010, ANGEW CHEM, V122, P8704
[10]
Total Synthesis and Determination of the Absolute Configuration of (-)-Dolabriferol
Laclef, Sylvain
论文数:
0
引用数:
0
h-index:
0
机构:
Swiss Fed Inst Technol EPFL, Lab Glycochim & Synth Asymetr, CH-1015 Lausanne, Switzerland
Swiss Fed Inst Technol EPFL, Lab Glycochim & Synth Asymetr, CH-1015 Lausanne, Switzerland
Laclef, Sylvain
Turks, Maris
论文数:
0
引用数:
0
h-index:
0
机构:
Riga Tech Univ, Fac Mat Sci & Appl Chem, LV-1658 Riga, Latvia
Swiss Fed Inst Technol EPFL, Lab Glycochim & Synth Asymetr, CH-1015 Lausanne, Switzerland
Turks, Maris
Vogel, Pierre
论文数:
0
引用数:
0
h-index:
0
机构:
Swiss Fed Inst Technol EPFL, Lab Glycochim & Synth Asymetr, CH-1015 Lausanne, Switzerland
Swiss Fed Inst Technol EPFL, Lab Glycochim & Synth Asymetr, CH-1015 Lausanne, Switzerland
Vogel, Pierre
[J].
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,
2010,
49
(45)
: 8525
-
8527
←
1
2
3
→