ArticleThe Journal of organic chemistry2013
Preparation of anti-vicinal amino alcohols: asymmetric synthesis of D-erythro-sphinganine, (+)-spisulosine, and D-ribo-phytosphingosine.
Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Unnatural C6-Substituted d-Galactosides as Attenuated Substrates of Glycosyl Hydrolases.Chembiochem : a European journal of chemical biology · 2026Article
- Ceramides: A Biologically Attractive Lipid and Advances in Acquisition Strategies.Antioxidants (Basel, Switzerland) · 2026Review
- Recent Progress in the Diverse Synthetic Approaches to Phytosphingosine.Topics in current chemistry (Cham) · 2025Review
- Photoredox catalysis harvesting multiple photon or electrochemical energies.Beilstein journal of organic chemistry · 2023Review
- Highly Selective Radical Relay 1,4-Oxyimination of Two Electronically Differentiated Olefins.Journal of the American Chemical Society · 2022Article
- Regiodivergent Electrophotocatalytic Aminooxygenation of Aryl Olefins.Journal of the American Chemical Society · 2022Article
- Stereoselective Synthesis of Novel Sphingoid Bases Utilized for Exploring the Secrets of Sphinx.International journal of molecular sciences · 2021Article
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3 authors.
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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, whereas the Overman rearrangement of chiral allylic trichloroacetimidates generated by the asymmetric reduction of an α,β-unsaturated methyl ketone allowed rapid access both to D-ribo-phytosphingosine and L-arabino-phytosphingosine.
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