Enantioselective Synthesis of (+)-Estrone Exploiting a Hydrogen Bond-Promoted Diels−Alder Reaction

[Image: see text] Starting from Dane’s diene and methylcyclopentenedione, (+)-estrone is synthesized along the Quinkert−Dane route in 24% total yield. The key step is an enantioselective Diels−Alder reaction promoted by an amidinium catalyst as efficiently as by a traditional Ti-TADDOLate Lewis acid...

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Autores principales: Weimar, Marko, Dürner, Gerd, Bats, Jan W., Göbel, Michael W.
Formato: Texto
Lenguaje:English
Publicado: American Chemical Society 2010
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2852147/
https://www.ncbi.nlm.nih.gov/pubmed/20302330
http://dx.doi.org/10.1021/jo100053j
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author Weimar, Marko
Dürner, Gerd
Bats, Jan W.
Göbel, Michael W.
author_facet Weimar, Marko
Dürner, Gerd
Bats, Jan W.
Göbel, Michael W.
author_sort Weimar, Marko
collection PubMed
description [Image: see text] Starting from Dane’s diene and methylcyclopentenedione, (+)-estrone is synthesized along the Quinkert−Dane route in 24% total yield. The key step is an enantioselective Diels−Alder reaction promoted by an amidinium catalyst as efficiently as by a traditional Ti-TADDOLate Lewis acid.
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spelling pubmed-28521472010-04-09 Enantioselective Synthesis of (+)-Estrone Exploiting a Hydrogen Bond-Promoted Diels−Alder Reaction Weimar, Marko Dürner, Gerd Bats, Jan W. Göbel, Michael W. J Org Chem [Image: see text] Starting from Dane’s diene and methylcyclopentenedione, (+)-estrone is synthesized along the Quinkert−Dane route in 24% total yield. The key step is an enantioselective Diels−Alder reaction promoted by an amidinium catalyst as efficiently as by a traditional Ti-TADDOLate Lewis acid. American Chemical Society 2010-03-19 2010-04-16 /pmc/articles/PMC2852147/ /pubmed/20302330 http://dx.doi.org/10.1021/jo100053j Text en Copyright © 2010 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org.
spellingShingle Weimar, Marko
Dürner, Gerd
Bats, Jan W.
Göbel, Michael W.
Enantioselective Synthesis of (+)-Estrone Exploiting a Hydrogen Bond-Promoted Diels−Alder Reaction
title Enantioselective Synthesis of (+)-Estrone Exploiting a Hydrogen Bond-Promoted Diels−Alder Reaction
title_full Enantioselective Synthesis of (+)-Estrone Exploiting a Hydrogen Bond-Promoted Diels−Alder Reaction
title_fullStr Enantioselective Synthesis of (+)-Estrone Exploiting a Hydrogen Bond-Promoted Diels−Alder Reaction
title_full_unstemmed Enantioselective Synthesis of (+)-Estrone Exploiting a Hydrogen Bond-Promoted Diels−Alder Reaction
title_short Enantioselective Synthesis of (+)-Estrone Exploiting a Hydrogen Bond-Promoted Diels−Alder Reaction
title_sort enantioselective synthesis of (+)-estrone exploiting a hydrogen bond-promoted diels−alder reaction
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2852147/
https://www.ncbi.nlm.nih.gov/pubmed/20302330
http://dx.doi.org/10.1021/jo100053j
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AT durnergerd enantioselectivesynthesisofestroneexploitingahydrogenbondpromoteddielsalderreaction
AT batsjanw enantioselectivesynthesisofestroneexploitingahydrogenbondpromoteddielsalderreaction
AT gobelmichaelw enantioselectivesynthesisofestroneexploitingahydrogenbondpromoteddielsalderreaction

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