Enantioselective Total Syntheses of Preussomerins: Control of Spiroacetal Stereogenicity by Photochemical Reaction of a Naphthoquinone through 1,6‐Hydrogen Atom Transfer

We report the enantioselective total syntheses of preussomerins EG(1), EG(2), and EG(3). The key transformation is a stereospecific photochemical reaction involving 1,6‐hydrogen atom transfer to achieve retentive replacement of a C−H with a C−O bond, enabling otherwise‐difficult control of the spiro...

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Autores principales: Ando, Yoshio, Ogawa, Daichi, Ohmori, Ken, Suzuki, Keisuke
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107447/
https://www.ncbi.nlm.nih.gov/pubmed/36446739
http://dx.doi.org/10.1002/anie.202213682
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author Ando, Yoshio
Ogawa, Daichi
Ohmori, Ken
Suzuki, Keisuke
author_facet Ando, Yoshio
Ogawa, Daichi
Ohmori, Ken
Suzuki, Keisuke
author_sort Ando, Yoshio
collection PubMed
description We report the enantioselective total syntheses of preussomerins EG(1), EG(2), and EG(3). The key transformation is a stereospecific photochemical reaction involving 1,6‐hydrogen atom transfer to achieve retentive replacement of a C−H with a C−O bond, enabling otherwise‐difficult control of the spiroacetal stereogenic center.
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spelling pubmed-101074472023-04-18 Enantioselective Total Syntheses of Preussomerins: Control of Spiroacetal Stereogenicity by Photochemical Reaction of a Naphthoquinone through 1,6‐Hydrogen Atom Transfer Ando, Yoshio Ogawa, Daichi Ohmori, Ken Suzuki, Keisuke Angew Chem Int Ed Engl Research Articles We report the enantioselective total syntheses of preussomerins EG(1), EG(2), and EG(3). The key transformation is a stereospecific photochemical reaction involving 1,6‐hydrogen atom transfer to achieve retentive replacement of a C−H with a C−O bond, enabling otherwise‐difficult control of the spiroacetal stereogenic center. John Wiley and Sons Inc. 2022-12-21 2023-01-26 /pmc/articles/PMC10107447/ /pubmed/36446739 http://dx.doi.org/10.1002/anie.202213682 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Ando, Yoshio
Ogawa, Daichi
Ohmori, Ken
Suzuki, Keisuke
Enantioselective Total Syntheses of Preussomerins: Control of Spiroacetal Stereogenicity by Photochemical Reaction of a Naphthoquinone through 1,6‐Hydrogen Atom Transfer
title Enantioselective Total Syntheses of Preussomerins: Control of Spiroacetal Stereogenicity by Photochemical Reaction of a Naphthoquinone through 1,6‐Hydrogen Atom Transfer
title_full Enantioselective Total Syntheses of Preussomerins: Control of Spiroacetal Stereogenicity by Photochemical Reaction of a Naphthoquinone through 1,6‐Hydrogen Atom Transfer
title_fullStr Enantioselective Total Syntheses of Preussomerins: Control of Spiroacetal Stereogenicity by Photochemical Reaction of a Naphthoquinone through 1,6‐Hydrogen Atom Transfer
title_full_unstemmed Enantioselective Total Syntheses of Preussomerins: Control of Spiroacetal Stereogenicity by Photochemical Reaction of a Naphthoquinone through 1,6‐Hydrogen Atom Transfer
title_short Enantioselective Total Syntheses of Preussomerins: Control of Spiroacetal Stereogenicity by Photochemical Reaction of a Naphthoquinone through 1,6‐Hydrogen Atom Transfer
title_sort enantioselective total syntheses of preussomerins: control of spiroacetal stereogenicity by photochemical reaction of a naphthoquinone through 1,6‐hydrogen atom transfer
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10107447/
https://www.ncbi.nlm.nih.gov/pubmed/36446739
http://dx.doi.org/10.1002/anie.202213682
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