Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1384633 | Carbohydrate Research | 2010 | 11 Pages |
Abstract
An approach to the stereocontrolled synthesis of the protected form of sphingofungin E (32) starting from the known protected d-glucose derivative 3 is described herein. For the construction of a tetrasubstituted carbon atom that is substituted with nitrogen, the [3,3]-sigmatropic rearrangement of thiocyanate 8 was employed. Subsequent functional group interconversions afforded the highly functionalized fragment, allylic bromide 26. Its coupling reaction with the known C12 hydrophobic segment 2, followed by further manipulation, completed the total synthesis.
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Related Topics
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Organic Chemistry
Authors
Miroslava Martinková, Jozef Gonda, Jana Špaková Raschmanová, Michaela Slaninková, Juraj Kuchár,