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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)
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Title
| - Enantioselective Synthesis of (-)-Methoxyestrone
- Enantioselective Synthesis of (-)-Methoxyestrone (en)
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skos:prefLabel
| - Enantioselective Synthesis of (-)-Methoxyestrone
- Enantioselective Synthesis of (-)-Methoxyestrone (en)
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skos:notation
| - RIV/00216208:11310/11:10104901!RIV12-MSM-11310___
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http://linked.open...avai/riv/aktivita
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http://linked.open...avai/riv/aktivity
| - P(1M0508), S, Z(MSM0021620857)
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http://linked.open...iv/cisloPeriodika
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http://linked.open...vai/riv/dodaniDat
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http://linked.open...aciTvurceVysledku
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http://linked.open.../riv/druhVysledku
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http://linked.open...iv/duvernostUdaju
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http://linked.open...titaPredkladatele
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http://linked.open...dnocenehoVysledku
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http://linked.open...ai/riv/idVysledku
| - RIV/00216208:11310/11:10104901
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http://linked.open...riv/jazykVysledku
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http://linked.open.../riv/klicovaSlova
| - construction; (+/-)-estrone; steroids; (+)-estrone; derivatives; estrone; arylboronic acids; meinwald rearrangement; diels-alder reaction; catalyzed asymmetric 1,4-addition (en)
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http://linked.open.../riv/klicoveSlovo
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http://linked.open...odStatuVydavatele
| - GB - Spojené království Velké Británie a Severního Irska
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http://linked.open...ontrolniKodProRIV
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http://linked.open...i/riv/nazevZdroje
| - European Journal of Organic Chemistry
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http://linked.open...in/vavai/riv/obor
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http://linked.open...ichTvurcuVysledku
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http://linked.open...cetTvurcuVysledku
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http://linked.open...vavai/riv/projekt
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http://linked.open...UplatneniVysledku
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http://linked.open...v/svazekPeriodika
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http://linked.open...iv/tvurceVysledku
| - Kotora, Martin
- Betík, Robert
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http://linked.open...ain/vavai/riv/wos
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http://linked.open...n/vavai/riv/zamer
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issn
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number of pages
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http://bibframe.org/vocab/doi
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http://localhost/t...ganizacniJednotka
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