Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B

Enantiomerically highly enriched unsaturated β-ketoesters bearing a quaternary stereocenter can be utilized as building blocks for the synthesis of natural occurring terpenes, i. a., trisporic acid and its derivatives. An advanced building block has been synthesized in a short reaction sequence, whi...

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Detalles Bibliográficos
Autores principales: Dubberke, Silke, Abbas, Muhammad, Westermann, Bernhard
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3079125/
https://www.ncbi.nlm.nih.gov/pubmed/21512603
http://dx.doi.org/10.3762/bjoc.7.54
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author Dubberke, Silke
Abbas, Muhammad
Westermann, Bernhard
author_facet Dubberke, Silke
Abbas, Muhammad
Westermann, Bernhard
author_sort Dubberke, Silke
collection PubMed
description Enantiomerically highly enriched unsaturated β-ketoesters bearing a quaternary stereocenter can be utilized as building blocks for the synthesis of natural occurring terpenes, i. a., trisporic acid and its derivatives. An advanced building block has been synthesized in a short reaction sequence, which involves an oxidative allylic rearrangement initiated by pyridinium dichromate (PDC) as the key step.
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spelling pubmed-30791252011-04-21 Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B Dubberke, Silke Abbas, Muhammad Westermann, Bernhard Beilstein J Org Chem Full Research Paper Enantiomerically highly enriched unsaturated β-ketoesters bearing a quaternary stereocenter can be utilized as building blocks for the synthesis of natural occurring terpenes, i. a., trisporic acid and its derivatives. An advanced building block has been synthesized in a short reaction sequence, which involves an oxidative allylic rearrangement initiated by pyridinium dichromate (PDC) as the key step. Beilstein-Institut 2011-04-11 /pmc/articles/PMC3079125/ /pubmed/21512603 http://dx.doi.org/10.3762/bjoc.7.54 Text en Copyright © 2011, Dubberke et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Dubberke, Silke
Abbas, Muhammad
Westermann, Bernhard
Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B
title Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B
title_full Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B
title_fullStr Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B
title_full_unstemmed Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B
title_short Oxidative allylic rearrangement of cycloalkenols: Formal total synthesis of enantiomerically pure trisporic acid B
title_sort oxidative allylic rearrangement of cycloalkenols: formal total synthesis of enantiomerically pure trisporic acid b
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3079125/
https://www.ncbi.nlm.nih.gov/pubmed/21512603
http://dx.doi.org/10.3762/bjoc.7.54
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AT westermannbernhard oxidativeallylicrearrangementofcycloalkenolsformaltotalsynthesisofenantiomericallypuretrisporicacidb

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