[Rapid Access to Enantiomerically Pure 3,6-Anhydro-2-deoxy-7-phenylglyconolactones. Synthesis of Diastereoisomers of (+)-Goniofufurone]

Title:[Rapid Access to Enantiomerically Pure 3,6-Anhydro-2-deoxy-7-phenylglyconolactones. Synthesis of Diastereoisomers of (+)-Goniofufurone]

Volume: 3 Issue: 7

Author(s): Leticia Quintero, Fernando Sartillo-Piscil, Silvano Cruz-Gregorio and Cristhian Sartillo-Melendez

Affiliation:

Abstract: 3,4-Anhydro-2-deoxy-7-phenylglyconolactones were synthesized in six steps from diacetone-Dglucose. Construction of the cis-fused bicyclic systems of the corresponding 3,4-anhydro-2-deoxy-7- phenylglycolactones was achieved by a stereoselective substitution reaction at the anomeric position of the 1,2-O-isopropylidene group of the corresponding 1,2-O-isopropylidenefuranose derivatives. Another important reaction was a sequential hydrolysis-oxidation-addition of Grignard reagent reaction. This reaction permits to place the phenyl group at C-7 position in “one pot” from diacetone-D-glucose.

Cite this article as:

Quintero Leticia, Sartillo-Piscil Fernando, Cruz-Gregorio Silvano and Sartillo-Melendez Cristhian, [Rapid Access to Enantiomerically Pure 3,6-Anhydro-2-deoxy-7-phenylglyconolactones. Synthesis of Diastereoisomers of (+)-Goniofufurone], Letters in Organic Chemistry 2006; 3 (7) . https://dx.doi.org/10.2174/157017806778341889