Dexter, H.R., Allen, E. and Williams, D.M. orcid.org/0000-0002-5618-182X (2018) A concise stereoselective synthesis of pterosin B. Tetrahedron Letters, 59 (49). pp. 4323-4325. ISSN 0040-4039
Abstract
Pterosin B is a naturally occurring indanone found in bracken fern (Pteridium aquilinum) that displays a variety of interesting pharmacological properties, but for which few stereoselective syntheses exist. Herein we describe a 7-step stereoselective synthesis of (2R)-pterosin B via 6-bromo-5,7-dimethylindan-1-one whose structure was confirmed by NOE analysis and structure determination by X-ray crystallography. The hydroxyethyl chain was introduced via a Suzuki-Miyaura cross-coupling reaction. The 2-methyl group was introduced stereoselectively by methylation of a SAMP [(S)-1-amino-2-methoxymethyl)pyrrolidine] hydrazone and the chiral auxiliary was removed to produce (2R)-pterosin B. The structure of pterosin B was confirmed by specific rotation and structural determination by X-ray crystallography.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2018 Published by Elsevier Ltd. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/). |
Keywords: | Pterosin B; Indanone; Suzuki-Miyaura reaction; SAMP |
Dates: |
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Institution: | The University of Sheffield |
Academic Units: | The University of Sheffield > Faculty of Science (Sheffield) > Department of Chemistry (Sheffield) |
Depositing User: | Symplectic Sheffield |
Date Deposited: | 06 Dec 2018 16:30 |
Last Modified: | 06 Dec 2018 16:30 |
Published Version: | https://doi.org/10.1016/j.tetlet.2018.10.056 |
Status: | Published |
Publisher: | Elsevier |
Refereed: | Yes |
Identification Number: | 10.1016/j.tetlet.2018.10.056 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:138843 |