Calder, E.D.D., Zaed, A.M. and Sutherland, A. (2013) Preparation of anti-vicinal amino alcohols: asymmetric synthesis of D-erythro-Sphinganine, (+)-spisulosine and D-ribo-phytosphingosine. Journal of Organic Chemistry, 78(14), pp. 7223-7233. (doi: 10.1021/jo401211j)
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Abstract
Two variations of the Overman rearrangement have been developed for the highly selective synthesis of anti-vicinal amino alcohol natural products. A MOM-ether directed palladium(II)-catalyzed rearrangement of an allylic trichloroacetimidate was used as the key step for the preparation of the protein kinase C inhibitor D-erythro-sphinganine and the antitumor agent (+)-spisulosine, while the Overman rearrangement of chiral allylic trichloroacetimidates generated by asymmetric reduction of an alpha,beta-unsaturated methyl ketone allowed rapid access to both D-ribo-phytosphingosine and L-arabino-phytosphingosine.
Item Type: | Articles |
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Status: | Published |
Refereed: | Yes |
Glasgow Author(s) Enlighten ID: | Zaed, Mr Ahmed Mohamed and Sutherland, Professor Andrew |
Authors: | Calder, E.D.D., Zaed, A.M., and Sutherland, A. |
College/School: | College of Science and Engineering > School of Chemistry |
Journal Name: | Journal of Organic Chemistry |
Publisher: | American Chemical Society |
ISSN: | 0022-3263 |
ISSN (Online): | 1520-6904 |
Copyright Holders: | Copyright © 2013 American Chemical Society |
First Published: | First published in Journal of Organic Chemistry 78(14):7223-7233 |
Publisher Policy: | Reproduced in accordance with the copyright policy of the publisher |
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