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Synthesis 2013; 45(23): 3276-3280
DOI: 10.1055/s-0033-1338545
DOI: 10.1055/s-0033-1338545
paper
Stereoselective Synthesis of (+)-Polyoxamic Acid Starting with a Chiral Aziridine
Weitere Informationen
Publikationsverlauf
Received: 27. August 2013
Accepted after revision: 13. September 2013
Publikationsdatum:
26. September 2013 (online)
Abstract
An efficient and stereoselective synthesis of (+)-polyoxamic acid was developed. The route starts with the commercially available 1-(R)-α-methylbenzylaziridine-2-methanol, a substance that has not been used previously as a starting material for the preparation of this target. The route also features the use of a stereocontrolled Sharpless asymmetric dihydroxylation reaction, promoted by AD-mix-α, which is followed by a regioselective aziridine ring-opening process, to generate the basic skeleton of target natural product. Subsequent oxidation and global deprotection produces (+)-polyoxamic acid.
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