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γ-Amino-β-keto Phosphonates in Synthesis: Synthesis of the Sphingosine Skeleton
| Content Provider | Scilit |
|---|---|
| Author | Krische, Michael J. |
| Editor | Koskinen, Ari M. P. |
| Copyright Year | 1990 |
| Description | Fully N,O-protected serine methyl ester [methyl (S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-oxazolidinecarboxylate] was converted with dimethyl lithiomethylphosphonate to the corres-ponding γ-amino-β-keto phosphonate [(S)-3-(tert-butoxycarbonyl)-4-[2-(dimethoxyphosphoryl)-1-oxoethyl]-2,2-dimethyloxazolidine]. This reacts with aldehydes under basic conditions $(K_{2}CO_{3}$) in high yields to generate the corresponding α′-amino-β′-hydroxy enone [(S)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-(1-oxo-2-alkenyl)oxazolidine]. The latter compounds can be elaborated to give sphingosine [2-amino-4-octadecene-1,3-diol] and its analogues. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-1990-21202.pdf |
| Ending Page | 666 |
| Page Count | 2 |
| Starting Page | 665 |
| ISSN | 09365214 |
| e-ISSN | 14372096 |
| DOI | 10.1055/s-1990-21202 |
| Journal | Synlett |
| Issue Number | 11 |
| Volume Number | 1990 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 1990-01-01 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synlett Organic Chemistry Amino Β Em Class |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry |
