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A novel methodology has been described, employing the RambergBcklund rearrangement to synthesize Cglycosides. The RambergBcklund sequence to provide Cglycosides includes three intermediates: thioglycoside, sulfonyl glycoside, and exoglycal. Thioglycosides can be easily made using different methods. Sulfone formation was routine with MMPP. The onepot RambergBcklund reaction of sulfone was done using C2Br2F4 , tBuOH and KOH/Al2O3 under reflux to afford an exoglycal intermediate. The beltaCglycosides can be made by hydrogenolysis of exoglycals using H2 and Pd/C. The alphaCglycosides can be made stereoselectively from exoglycals via intramolecular ionic hydrogenation as the key step. Some of the C glycerolipids that have been prepared exhibit strikingly similar in vitro antiproliferative effects to those of Oglycoside analogs.
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