Stereoselective Synthesis of (+)-Polyoxamic Acid Starting with a Chiral Aziridine
- Stereoselective Synthesis of (+)-Polyoxamic Acid Starting with a Chiral Aziridine
- 윤호종; 심태보
- (+)-Polyoxamic Acid; polyhydroxylated amino acid; natural product synthesis; chiral aziridine; asymmetric dihydroxylation
- Issue Date
- VOL 45, NO 23, 3276-3280
- 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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