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Statements

Subject Item
n2:RIV%2F00216208%3A11310%2F11%3A10104901%21RIV12-MSM-11310___
rdf:type
n5:Vysledek skos:Concept
rdfs:seeAlso
http://dx.doi.org/10.1002/ejoc.201100317
dcterms:description
Enantioselective synthesis of unnatural (-)-methoxyestrone in 12 steps from the commercially available tetralone based on the formation of a chiral bicyclic intermediate having the A-B steroid ring framework was accomplished. The crucial synthetic step comprised the enantioselective conjugate addition of vinylmagnesium bromide to a chiral imine formed from a trisubstituted cyclic alpha,beta-unsaturated aldehyde with }98% ee, giving rise to the stereoselectively substituted building block possessing the A-B steroid rings. Further steps included the construction of the side chain containing the triple bond, and the obtained enyne was subjected to a Pauson-Khand reaction that furnished stereoselectively an intermediate tetracyclic ketone. Further functional group transformations yielded the target compound. Enantioselective synthesis of unnatural (-)-methoxyestrone in 12 steps from the commercially available tetralone based on the formation of a chiral bicyclic intermediate having the A-B steroid ring framework was accomplished. The crucial synthetic step comprised the enantioselective conjugate addition of vinylmagnesium bromide to a chiral imine formed from a trisubstituted cyclic alpha,beta-unsaturated aldehyde with }98% ee, giving rise to the stereoselectively substituted building block possessing the A-B steroid rings. Further steps included the construction of the side chain containing the triple bond, and the obtained enyne was subjected to a Pauson-Khand reaction that furnished stereoselectively an intermediate tetracyclic ketone. Further functional group transformations yielded the target compound.
dcterms:title
Enantioselective Synthesis of (-)-Methoxyestrone Enantioselective Synthesis of (-)-Methoxyestrone
skos:prefLabel
Enantioselective Synthesis of (-)-Methoxyestrone Enantioselective Synthesis of (-)-Methoxyestrone
skos:notation
RIV/00216208:11310/11:10104901!RIV12-MSM-11310___
n5:predkladatel
n12:orjk%3A11310
n3:aktivita
n7:Z n7:S n7:P
n3:aktivity
P(1M0508), S, Z(MSM0021620857)
n3:cisloPeriodika
18
n3:dodaniDat
n9:2012
n3:domaciTvurceVysledku
n8:7832435 n8:4268180
n3:druhVysledku
n14:J
n3:duvernostUdaju
n22:S
n3:entitaPredkladatele
n20:predkladatel
n3:idSjednocenehoVysledku
197433
n3:idVysledku
RIV/00216208:11310/11:10104901
n3:jazykVysledku
n13:eng
n3:klicovaSlova
construction; (+/-)-estrone; steroids; (+)-estrone; derivatives; estrone; arylboronic acids; meinwald rearrangement; diels-alder reaction; catalyzed asymmetric 1,4-addition
n3:klicoveSlovo
n6:meinwald%20rearrangement n6:4-addition n6:%28%2B%29-estrone n6:%28%2B%2F-%29-estrone n6:steroids n6:catalyzed%20asymmetric%201 n6:arylboronic%20acids n6:estrone n6:diels-alder%20reaction n6:derivatives n6:construction
n3:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n3:kontrolniKodProRIV
[EC86CCE9BD33]
n3:nazevZdroje
European Journal of Organic Chemistry
n3:obor
n17:CC
n3:pocetDomacichTvurcuVysledku
2
n3:pocetTvurcuVysledku
2
n3:projekt
n4:1M0508
n3:rokUplatneniVysledku
n9:2011
n3:svazekPeriodika
2011
n3:tvurceVysledku
Betík, Robert Kotora, Martin
n3:wos
000291583700002
n3:zamer
n18:MSM0021620857
s:issn
1434-193X
s:numberOfPages
4
n21:doi
10.1002/ejoc.201100317
n16:organizacniJednotka
11310