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General strategy for a short and efficient synthesis of 3-hydroxy-4-methylprolines (HMP) |
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| Authors: | Debendra K Mohapatra Dhananjoy Mondal Mukund S Chorghade Mukund K Gurjar |
| Institution: | aDivision of Organic Chemistry: Technology, National Chemical Laboratory, Pune 411 008, India bChorghade Enterprises, 14, Carlson Circle, Natick, MA 01760, USA |
| Abstract: | The non-proteinogenic amino acid 3-hydroxy-4-methylproline (HMP) is an active constituent of some potent antimicrobials including echinocandins, nostopeptins, pneumocandins, sporiofungin and mulundocandins. A synthesis has been achieved in 10 steps with 29% overall yield; the Evans’ aldol reaction using Crimmins’ modified method was pivotal to the success of the strategy. |
| Keywords: | Garner’s aldehyde Crimmins’ aldol reaction Non-proteinogenic amino acids 3 4-Disubstituted proline RuO4 mediated oxidation |
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