Asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine, jaspine B (pachastrissamine), 2-epi-jaspine B, and deoxoprosophylline via lithium amide conjugate addition

Organic & Biomolecular Chemistry
Elin AbrahamJames E Thomson

Abstract

The highly diastereoselective anti-aminohydroxylation of (E)-gamma-tri-iso-propylsilyloxy-alpha,beta-unsaturated esters, via conjugate addition of lithium (S)-N-benzyl-N-(alpha-methylbenzyl)amide and subsequent in situ enolate oxidation with (+)-(camphorsulfonyl)oxaziridine, has been used as the key step in the asymmetric synthesis of N,O,O,O-tetra-acetyl d-lyxo-phytosphingosine (20% yield over 7 steps), the anhydrophytosphingosine jaspine B (10% yield over 9 steps), 2-epi-jaspine B (14% yield over 9 steps), and the Prosopis alkaloid deoxoprosophylline (26% yield over 7 steps).

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Citations

Jun 10, 2010·The Journal of Organic Chemistry·Zheng LiuRobert Bittman
Jan 9, 2010·Bioscience, Biotechnology, and Biochemistry·Hiroyuki UranoShigefumi Kuwahara
Feb 3, 2016·Chemical & Pharmaceutical Bulletin·Tomoya FujiwaraTakayuki Yakura
Feb 20, 2016·Carbohydrate Research·Eva MezeiováGabriela Gönciová
Jan 26, 2011·Organic & Biomolecular Chemistry·Mikko Passiniemi, Ari M P Koskinen
Oct 10, 2008·Organic & Biomolecular Chemistry·Caroline AciroJames E Thomson
Aug 19, 2018·Carbohydrate Research·Jana Špaková RaschmanováDávid Jáger
Apr 23, 2010·The Journal of Organic Chemistry·Yuji YoshimitsuHiroaki Ohno
Aug 1, 2009·The Journal of Organic Chemistry·Christopher W BondJames E Thomson
Jul 26, 2012·The Journal of Organic Chemistry·Alexander J CresswellJames E Thomson
Feb 6, 2013·The Journal of Organic Chemistry·Stephen G DaviesJames E Thomson
Jun 28, 2011·Carbohydrate Research·Miroslava MartinkováJuraj Kuchár

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