• Je něco špatně v tomto záznamu ?

Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps

PR. Jagtap, I. Císařová, U. Jahn,

. 2018 ; 16 (5) : 750-755.

Jazyk angličtina Země Anglie, Velká Británie

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/bmc19012942

A very short three-step approach to trans,trans,trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to α,β-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by single electron oxidation. The resulting 2,3-dialkyl-1,4-diketones form with moderate to good d/l-diastereoselectivity and are transformed to the target tetrahydrofuran lignans by reduction and diastereoselective cycloetherification.

Citace poskytuje Crossref.org

000      
00000naa a2200000 a 4500
001      
bmc19012942
003      
CZ-PrNML
005      
20190418081518.0
007      
ta
008      
190405s2018 enk f 000 0|eng||
009      
AR
024    7_
$a 10.1039/c7ob02848b $2 doi
035    __
$a (PubMed)29308468
040    __
$a ABA008 $b cze $d ABA008 $e AACR2
041    0_
$a eng
044    __
$a enk
100    1_
$a Jagtap, Pratap R $u Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo náměstí 2, 166 10 Prague, Czech Republic. ullrich.jahn@uochb.cas.cz.
245    10
$a Bioinspired total synthesis of tetrahydrofuran lignans by tandem nucleophilic addition/redox isomerization/oxidative coupling and cycloetherification reactions as key steps / $c PR. Jagtap, I. Císařová, U. Jahn,
520    9_
$a A very short three-step approach to trans,trans,trans-2,5-diaryl-3,4-dimethyltetrahydrofuran lignans is reported. The carbon skeleton is assembled in a single step based on an unprecedented tandem reaction consisting of 1,2-addition of aryllithium reagents to α,β-unsaturated aldehydes, ruthenium-catalyzed redox isomerization of the resulting alkoxides to enolates and their dimerization triggered by single electron oxidation. The resulting 2,3-dialkyl-1,4-diketones form with moderate to good d/l-diastereoselectivity and are transformed to the target tetrahydrofuran lignans by reduction and diastereoselective cycloetherification.
650    _2
$a aldehydy $x chemická syntéza $x chemie $7 D000447
650    _2
$a biomimetika $7 D032701
650    _2
$a katalýza $7 D002384
650    _2
$a techniky syntetické chemie $7 D060326
650    _2
$a krystalografie rentgenová $7 D018360
650    _2
$a cyklizace $7 D003500
650    _2
$a furany $x chemická syntéza $x chemie $7 D005663
650    _2
$a isomerie $7 D007536
650    _2
$a lignany $x chemická syntéza $x chemie $7 D017705
650    _2
$a molekulární modely $7 D008958
650    _2
$a oxidace-redukce $7 D010084
650    _2
$a oxidační párování $7 D058451
650    _2
$a ruthenium $x chemie $7 D012428
655    _2
$a časopisecké články $7 D016428
700    1_
$a Císařová, Ivana
700    1_
$a Jahn, Ullrich
773    0_
$w MED00007088 $t Organic & biomolecular chemistry $x 1477-0539 $g Roč. 16, č. 5 (2018), s. 750-755
856    41
$u https://pubmed.ncbi.nlm.nih.gov/29308468 $y Pubmed
910    __
$a ABA008 $b sig $c sign $y a $z 0
990    __
$a 20190405 $b ABA008
991    __
$a 20190418081545 $b ABA008
999    __
$a ok $b bmc $g 1392252 $s 1051247
BAS    __
$a 3
BAS    __
$a PreBMC
BMC    __
$a 2018 $b 16 $c 5 $d 750-755 $i 1477-0539 $m Organic & biomolecular chemistry $n Org Biomol Chem $x MED00007088
LZP    __
$a Pubmed-20190405

Najít záznam

Citační ukazatele

Možnosti archivace