Enantioselective Synthesis of (-)-Methoxyestrone
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F11%3A10104901" target="_blank" >RIV/00216208:11310/11:10104901 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201100317" target="_blank" >http://dx.doi.org/10.1002/ejoc.201100317</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201100317" target="_blank" >10.1002/ejoc.201100317</a>
Alternative languages
Result language
angličtina
Original language name
Enantioselective Synthesis of (-)-Methoxyestrone
Original language 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 theA-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.
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/1M0508" target="_blank" >1M0508: New Antivirals and Antineoplastics</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)<br>Z - Vyzkumny zamer (s odkazem do CEZ)<br>S - Specificky vyzkum na vysokych skolach
Others
Publication year
2011
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
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Volume of the periodical
2011
Issue of the periodical within the volume
18
Country of publishing house
GB - UNITED KINGDOM
Number of pages
4
Pages from-to
3279-3282
UT code for WoS article
000291583700002
EID of the result in the Scopus database
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