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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
Nagamalla, Someshwar Paul, Debobrata Mague, Joel T. Sathyamoorthi, Shyam
Nagamalla, Someshwar
Paul, Debobrata
Mague, Joel T.
Sathyamoorthi, Shyam
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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.
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.
Date
2022-08-11
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American Chemical Society
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Keywords
Alcohols, Aziridines, Cyclization, Ethers, Pharmaceuticals
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