One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes

An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of ortho-fused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation. Various derivatives could be obtained from commercially available (hetero...

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Detalles Bibliográficos
Autores principales: Burroughs, Laurence, Eccleshare, Lee, Ritchie, John, Kulkarni, Omkar, Lygo, Barry, Woodward, Simon, Lewis, William
Formato: Online Artículo Texto
Lenguaje:English
Publicado: WILEY-VCH Verlag 2015
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4581465/
https://www.ncbi.nlm.nih.gov/pubmed/26230528
http://dx.doi.org/10.1002/anie.201505347
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author Burroughs, Laurence
Eccleshare, Lee
Ritchie, John
Kulkarni, Omkar
Lygo, Barry
Woodward, Simon
Lewis, William
author_facet Burroughs, Laurence
Eccleshare, Lee
Ritchie, John
Kulkarni, Omkar
Lygo, Barry
Woodward, Simon
Lewis, William
author_sort Burroughs, Laurence
collection PubMed
description An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of ortho-fused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields.
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spelling pubmed-45814652015-09-29 One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes Burroughs, Laurence Eccleshare, Lee Ritchie, John Kulkarni, Omkar Lygo, Barry Woodward, Simon Lewis, William Angew Chem Int Ed Engl Communications An intramolecular Cannizzaro-type hydride transfer to an in situ prepared allene enables the synthesis of ortho-fused 4-substituted cycloocta-2,5-dien-1-ones with unprecedented technical ease for an eight-ring carboannulation. Various derivatives could be obtained from commercially available (hetero)aryl aldehydes, trimethylsilylacetylene, and simple propargyl chlorides in good yields. WILEY-VCH Verlag 2015-09-01 2015-07-29 /pmc/articles/PMC4581465/ /pubmed/26230528 http://dx.doi.org/10.1002/anie.201505347 Text en © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. https://creativecommons.org/licenses/by/4.0/ © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Burroughs, Laurence
Eccleshare, Lee
Ritchie, John
Kulkarni, Omkar
Lygo, Barry
Woodward, Simon
Lewis, William
One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes
title One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes
title_full One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes
title_fullStr One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes
title_full_unstemmed One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes
title_short One-Pot Cannizzaro Cascade Synthesis of ortho-Fused Cycloocta-2,5-dien-1-ones from 2-Bromo(hetero)aryl Aldehydes
title_sort one-pot cannizzaro cascade synthesis of ortho-fused cycloocta-2,5-dien-1-ones from 2-bromo(hetero)aryl aldehydes
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4581465/
https://www.ncbi.nlm.nih.gov/pubmed/26230528
http://dx.doi.org/10.1002/anie.201505347
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