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

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

Journal Name: Letters in Organic Chemistry

Volume 3 , Issue 7 , 2006

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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.

Keywords: one pot, oxocarbenium ions, Woerpel's model, Diastereoisomers of Goniofufurone

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Article Details

VOLUME: 3
ISSUE: 7
Year: 2006
Page: [504 - 509]
Pages: 6
DOI: 10.2174/157017806778341889
Price: $58

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