About: Enantioselective Synthesis of (-)-Methoxyestrone

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
rdfs:seeAlso	http://dx.doi.org/10.1002/ejoc.201100317
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. (en)
Title	Enantioselective Synthesis of (-)-Methoxyestrone Enantioselective Synthesis of (-)-Methoxyestrone (en)
skos:prefLabel	Enantioselective Synthesis of (-)-Methoxyestrone Enantioselective Synthesis of (-)-Methoxyestrone (en)
skos:notation	RIV/00216208:11310/11:10104901!RIV12-MSM-11310___
http://linked.open...avai/riv/aktivita	P S Z
http://linked.open...avai/riv/aktivity	P(1M0508), S, Z(MSM0021620857)
http://linked.open...iv/cisloPeriodika	18
http://linked.open...vai/riv/dodaniDat	2012
http://linked.open...aciTvurceVysledku	Betík, Robert Kotora, Martin
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Univerzita Karlova v Praze / Přírodovědecká fakulta
http://linked.open...dnocenehoVysledku	197433
http://linked.open...ai/riv/idVysledku	RIV/00216208:11310/11:10104901
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	construction; (+/-)-estrone; steroids; (+)-estrone; derivatives; estrone; arylboronic acids; meinwald rearrangement; diels-alder reaction; catalyzed asymmetric 1,4-addition (en)
http://linked.open.../riv/klicoveSlovo	(+)-estrone (+/-)-estrone 4-addition catalyzed asymmetric 1 diels-alder reaction estrone meinwald rearrangement steroids construction derivatives arylboronic acids
http://linked.open...odStatuVydavatele	GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV	[EC86CCE9BD33]
http://linked.open...i/riv/nazevZdroje	European Journal of Organic Chemistry
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	2 (xsd:int)
http://linked.open...cetTvurcuVysledku	2 (xsd:int)
http://linked.open...vavai/riv/projekt	New Antivirals and Antineoplastics
http://linked.open...UplatneniVysledku	2011
http://linked.open...v/svazekPeriodika	2011
http://linked.open...iv/tvurceVysledku	Kotora, Martin Betík, Robert
http://linked.open...ain/vavai/riv/wos	000291583700002
http://linked.open...n/vavai/riv/zamer	Nové molekulární systémy pro pokročilé aplikace prospěšné pro zdraví a šetrné k životnímu prostředí
issn	1434-193X
number of pages	4 (xsd:int)
http://bibframe.org/vocab/doi	10.1002/ejoc.201100317
http://localhost/t...ganizacniJednotka	11310

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