| Abstract
| - A novel strategy for the synthesis of d,l-glucosylceramide 1, a member of the glycosphingolipidclass of natural products is described. Reagent-controlled asymmetric Brown allylboration gaveexcellent stereochemical control in the construction of adjacent stereocenters in the sphingoid baseportion of the molecule. The trans-configured double bond was obtained as a single geometricalisomer by use of silicon-tethered olefin metathesis employing the Schrock carbene [(CF3)2MeCO]2Mo(CHCMe2Ph)(NC6H3-2,6-i-Pr2) and in situ PhLi-induced ring-opening of the intermediate 5,6-dihydro-2H-1,2-oxasiline followed by protodesilylation with TBAF in DMSO. The synthesis wascompleted by long chain amide formation and global deprotection.
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