D. Hotchkiss, R. Soengas, M. Simone
Dec 13, 2004
Citations
0
Influential Citations
53
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Protected branched sugar lactones are available via Kiliani-acetonation sequences on readily available ketoses such as d -fructose and l -sorbose. In both cases, the readily crystallized diacetonides have a 2,3- cis -diol relationship in the product lactone. An efficient double inversion of the configuration at C-4 and C-5 of the product from d -fructose gives access to the formal Kiliani product from l -psicose. Branched carbohydrate lactones are likely to be of significant value as chirons for homochiral targets with functionalized quaternary centres.