A general, efficient and stereospecific route to sphingosine, sphinganines, phytosphingosines and their analogs

Organic & Biomolecular Chemistry
Ye CaiDavid R Bundle

Abstract

Sphingosine, sphinganines and phytosphingosines and their analogs were synthesized by an aldol condensation between an iminoglycinate bearing a (+)-(1R,2R,5R)-2-hydroxy-3-pinanone group as chiral auxiliary and an appropriate aldehyde. All condensations proceeded with excellent enantioselectivity to generate the (2S,3R)-D-erythro structures in good yields.

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Citations

Apr 30, 2011·Future Medicinal Chemistry·Chang-Chun Ling, David R Bundle
May 10, 2011·The Journal of Chemical Physics·C M WolfeJ Huennekens
Apr 19, 2008·Organic & Biomolecular Chemistry·Elin AbrahamAndrew D Smith
Apr 18, 2008·ChemMedChem·Matthias TrappeniersSerge Van Calenbergh
Nov 29, 2008·Organic & Biomolecular Chemistry·José Antonio Morales-SernaSergio Castillón
Feb 19, 2010·Organic & Biomolecular Chemistry·Fiona J Black, Philip J Kocienski
Aug 19, 2018·Carbohydrate Research·Jana Špaková RaschmanováDávid Jáger
Oct 29, 2009·The Journal of Organic Chemistry·Mahendra S SandbhorChristopher W Cairo
Aug 14, 2009·The Journal of Organic Chemistry·Catherine SéguinAlejandro Pérez-Luna
Jul 8, 2009·Journal of Medicinal Chemistry·Vivien LacôneDidier Dubreuil
Jun 29, 2010·The Journal of Organic Chemistry·Ramzi Ait-YoucefChristine Greck
May 9, 2014·The Journal of Organic Chemistry·Carlo SicilianoAndrea Temperini

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