Journal
TETRAHEDRON LETTERS
Volume 50, Issue 12, Pages 1273-1275Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.12.103
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Funding
- National Science Foundation [CH-0809143]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0809143] Funding Source: National Science Foundation
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erythro-Hydroxyasparagine (eHyAsn, 1) occurs ill a number of naturally occurring peptides and proteins. Previous syntheses have relied on enzyme-catalyzed reactions to produce relevant, optically active intermediates. We report herein a completely chemical synthesis that intercepts Boger's synthesis of the diastereomer (tHyAsn, 4), utilizing a Sharpless asymmetric aminohydroxylation reaction to introduce the two stereocenters. Boc-HyAsn(OTBS)-OH (10) was Coupled effectively with phenylalanine methyl ester using EDC/HOBt. (C) 2009 Elsevier Ltd. All rights reserved.
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