Divergent synthesis of D-erythro-sphingosine, L-threo-sphingosine, and their regioisomers
- PMID: 12636430
- DOI: 10.1021/jo0268254
Divergent synthesis of D-erythro-sphingosine, L-threo-sphingosine, and their regioisomers
Abstract
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.
Similar articles
-
A practical synthesis of D-erythro-sphingosine using a cross-metathesis approach.Org Biomol Chem. 2004 Jun 7;2(11):1643-6. doi: 10.1039/b403568b. Epub 2004 Apr 20. Org Biomol Chem. 2004. PMID: 15162217
-
Dihydroxylation of 2-vinylaziridine: efficient synthesis of D-ribo-phytosphingosine.Chem Commun (Camb). 2007 Jan 7;(1):79-81. doi: 10.1039/b612740a. Epub 2006 Nov 17. Chem Commun (Camb). 2007. PMID: 17279267
-
Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from D-ribo-(2S,3S,4R)-phytosphingosine.J Org Chem. 2004 Aug 20;69(17):5699-704. doi: 10.1021/jo049277y. J Org Chem. 2004. PMID: 15307742
-
Vinyl-, propargyl-, and allenylsilicon reagents in asymmetric synthesis: a relatively untapped resource of environmentally benign reagents.Chemistry. 2009;15(22):5402-16. doi: 10.1002/chem.200900337. Chemistry. 2009. PMID: 19421982 Review.
-
The nitroso ene reaction: a regioselective and stereoselective allylic nitrogen functionalization of mechanistic delight and synthetic potential.Chem Rev. 2003 Oct;103(10):4131-46. doi: 10.1021/cr030004x. Chem Rev. 2003. PMID: 14531720 Review. No abstract available.
Cited by
-
Aziridine Ring Opening as Regio- and Stereoselective Access to C-Glycosyl-Aminoethyl Sulfide Derivatives.Molecules. 2022 Mar 8;27(6):1764. doi: 10.3390/molecules27061764. Molecules. 2022. PMID: 35335129 Free PMC article.
-
Synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000), and their biological evaluation.Bioorg Med Chem. 2011 Jan 1;19(1):221-8. doi: 10.1016/j.bmc.2010.11.032. Epub 2010 Nov 19. Bioorg Med Chem. 2011. PMID: 21145749 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources