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Stereoselektive Hydrid‐Reduktion von Tetronsäurederivaten. Synthese verzweigtkettiger Tetrofuranosen
Author(s) -
Wyss Heinz,
Vögeli Ulrich,
Scheffold Rolf
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640317
Subject(s) - chemistry , stereoselectivity , stereochemistry , hydride , nuclear magnetic resonance spectroscopy , medicinal chemistry , organic chemistry , catalysis , metal
Stereoselective Hydride Reduction of Tetronic Acid Derivatives, Synthesis of Branched‐Chain Tetrofuranoses The 3‐methoxymethyl derivatives of 2‐methyl‐ D , L ‐threofuranose ( 10a ) and 2‐deoxy‐2‐methyl‐ D , L ‐erythrofuranose ( 11a ) are prepared starting from 2‐methyl‐tetronic acid ( 1 ). The key step is the stereoselective reduction of the 3‐oxo‐function of 2‐chloro‐2‐methyl‐3‐oxo‐γ‐butyrolacton ( 2 ) by sodiumborohydride, which proceeds predominantly anti with respect to the C,Cl‐bond. The configuration of the reduction products has been established by 1 H‐ and 13 C‐NMR.‐spectroscopy.