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Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-N-Hexanoyldihydrosphingosine
| dc.contributor.author | Nagamalla, Someshwar | |
| dc.contributor.author | Paul, Debobrata | |
| dc.contributor.author | Mague, Joel T. | |
| dc.contributor.author | Sathyamoorthi, Shyam | |
| dc.date.accessioned | 2023-06-13T20:16:19Z | |
| dc.date.available | 2023-06-13T20:16:19Z | |
| dc.date.issued | 2022-08-11 | |
| dc.identifier.citation | Nagamalla, S., Paul, D., Mague, J. T., & Sathyamoorthi, S. (2022). Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-N-Hexanoyldihydrosphingosine. Organic letters, 24(33), 6202–6207. https://doi.org/10.1021/acs.orglett.2c02496 | en_US |
| dc.identifier.uri | https://hdl.handle.net/1808/34372 | |
| dc.description | This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, Copyright © 2022 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.2c02496. | en_US |
| dc.description.abstract | We present a unique strategy for the synthesis of vicinal amino alcohols. Ring opening of aziridines with pendant silanols is compatible with a range of substrates. To engage productively in ring opening, the aziridine must be at least mildly activated, and a variety of such N-substituents are tolerated. The utility of this methodology is highlighted in facile preparations of the natural products (±)-Clavaminol H, (±)-dihydrosphingosine, and (±)-N-hexanoyldihydrosphingosine as well as a natural product analogue (±)-des-acetyl-Clavaminol H. | en_US |
| dc.publisher | American Chemical Society | en_US |
| dc.rights | Copyright © 2022 American Chemical Society | en_US |
| dc.subject | Alcohols | en_US |
| dc.subject | Aziridines | en_US |
| dc.subject | Cyclization | en_US |
| dc.subject | Ethers | en_US |
| dc.subject | Pharmaceuticals | en_US |
| dc.title | Ring Opening of Aziridines by Pendant Silanols Allows for Preparations of (±)-Clavaminol H, (±)-Des-Acetyl-Clavaminol H, (±)-Dihydrosphingosine, and (±)-N-Hexanoyldihydrosphingosine | en_US |
| dc.type | Article | en_US |
| kusw.kuauthor | Nagamalla, Someshwar | |
| kusw.kuauthor | Paul, Debobrata | |
| kusw.kuauthor | Mague, Joel T. | |
| kusw.kuauthor | Sathyamoorthi, Shyam | |
| kusw.kudepartment | Medicinal Chemistry | en_US |
| dc.identifier.doi | 10.1021/acs.orglett.2c02496 | en_US |
| dc.identifier.orcid | https://orcid.org/0000-0002-5270-7177 | en_US |
| dc.identifier.orcid | https://orcid.org/0000-0003-4705-7349 | en_US |
| kusw.oaversion | Scholarly/refereed, author accepted manuscript | en_US |
| kusw.oapolicy | This item meets KU Open Access policy criteria. | en_US |
| dc.identifier.pmid | PMC10017055 | en_US |
| dc.rights.accessrights | embargoedAccess | en_US |
