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Divergent synthesis of D-erythro-sphingosine, L-threo-sphingosine, and their regioisomers
KTH, Superseded Departments, Chemistry.
2003 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 68, no 6, 2514-2517 p.Article in journal (Refereed) Published
Abstract [en]

Starting from a vinyl epoxide, a divergent synthesis of four sphingosine isomers is described. The remaining four isomers can easily be synthesized using the same methodology. Although numerous syntheses of sphingosine have been published, this is the first general route leading to all eight isomers in this important compound class. The synthetic strategy relies on regioselective opening of a vinyl epoxide and a vinylaziridine in the allylic position.

Place, publisher, year, edition, pages
2003. Vol. 68, no 6, 2514-2517 p.
Keyword [en]
beta-amino alcohols, stereoselective synthesis, enantioselective synthesis, l-serine, route, regiodivergent, derivatives, products
Identifiers
URN: urn:nbn:se:kth:diva-22336DOI: 10.1021/jo0268254ISI: 000181639300067OAI: oai:DiVA.org:kth-22336DiVA: diva2:341034
Note
QC 20100525Available from: 2010-08-10 Created: 2010-08-10 Last updated: 2017-12-12Bibliographically approved

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