Asymmetric synthesis of vicinal amino alcohols: xestoaminol C, sphinganine and sphingosine

Organic & Biomolecular Chemistry
Elin AbrahamAndrew D Smith

Abstract

The highly diastereoselective anti-aminohydroxylation of 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-diacetyl xestoaminol C (41% yield over 8 steps), N,O,O-triacetyl sphinganine (30% yield over 8 steps) and N,O,O-triacetyl sphingosine (30% yield over 7 steps).

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Citations

Jul 28, 2015·Organic & Biomolecular Chemistry·Vineet Jeena, Ross S Robinson
Nov 29, 2008·Organic & Biomolecular Chemistry·José Antonio Morales-SernaSergio Castillón
Apr 28, 2009·ChemSusChem·Sebastian BähnMatthias Beller
Oct 10, 2008·Organic & Biomolecular Chemistry·Caroline AciroJames E Thomson
Jan 21, 2017·Organic & Biomolecular Chemistry·Mathieu EsgulianDavid J Aitken
Jan 6, 2011·Chemistry : a European Journal·Timothy J DonohoeAkshat H Rathi
Aug 1, 2009·The Journal of Organic Chemistry·Christopher W BondJames E Thomson
Jun 29, 2010·The Journal of Organic Chemistry·Ramzi Ait-YoucefChristine Greck
Aug 11, 2021·Journal of the American Chemical Society·Emily M MumfordScott E Denmark
May 9, 2014·The Journal of Organic Chemistry·Carlo SicilianoAndrea Temperini
Apr 6, 2013·Organic Letters·Stephen G DaviesJames E Thomson
Oct 1, 2011·European Journal of Medicinal Chemistry·Bi-Shuang ChenPei-Qiang Huang

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