Synthesis of 2-substituted (+/-)-(2R, 3R, 5R)-tetrahydrofuran-3,5-dicarboxylic acid derivatives

Authors
Wang, GT Wang, SD Chen, YW Gentles, R Sowin, T
Citation
Gt. Wang et al., Synthesis of 2-substituted (+/-)-(2R, 3R, 5R)-tetrahydrofuran-3,5-dicarboxylic acid derivatives, J ORG CHEM, 66(6), 2001, pp. 2052-2056
Citations number
43
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
66
Issue
6
Year of publication
2001
Pages
2052 - 2056
Database
ISI
SICI code
0022-3263(20010323)66:6<2052:SO2(35>2.0.ZU;2-F
Abstract
An efficient synthesis of 2-substituted (+/-)-(2R, 3R, 5R)-tetrahydrofuran- 3,5-dicarboxylic acid derivatives has been developed. Starting from 5-norbo rne-2-ol, the key intermediate (+/-)-methyl 5,6-exo,exo (isopropylidenediox y)-2-oxabicyclo [2.2.1]heptane-3-exo-carboxylate (15) was synthesized in an efficient six-step sequence. The key transformation is the base-catalyzed methanolysis-rearrangement of (+/-)-6,7-exo,exo-(isopropylidenedioxy)-4-exo -iodo-2-oxyabicyclo[3.2.1]octan-3-one (14). Further manipulation of the 3-s ubstituent of (+/-)-methyl 5,6-exe,exo-(isopropylidenedioxy)-2-oxabicyclo[2 .2.1] heptane-3-exo-carboxylate (15) followed by deprotection of the diol m oiety and ring opening catalyzed by RuCl3/NaIO4 gave the title compounds in good yield.