Bibliographic Details
| Title: |
An Efficient Enantioselective Synthesis of (2R)-Hydroxymethyl Glutamic Acid and an Approach to the (2R)-Hydroxymethyl-Substituted Sphingofungins. |
| Authors: |
Hayes, Christopher J.1 chris.hayes@nottingham.ac.uk, Bradley, Daniel M.1, Thomson, Nicholas M.2 |
| Source: |
Journal of Organic Chemistry. 3/31/2006, Vol. 71 Issue 7, p2661-2665. 5p. 4 Diagrams. |
| Subjects: |
Enantioselective catalysis, Methanol, Glutamic acid, Aldehydes, Carbenes, Natural products, Organic chemistry |
| Abstract: |
We have developed a short enantioselective synthesis of (2R)-hydroxymethyl glutamic acid (HMG) starting from Garner's aldehyde using an alkylidene carbene 1,5-CH insertion as a method to construct the quaternary stereocenter. A variety of conditions were examined for the oxidative cleavage of the key cyclopentene intermediate and we found that RuC13/NalO4 led directly to the desired amino bis-acid product. We were also able to show that oxidative cleavage of the cyclopentene 1,5-CH insertion product could be used to produce the amino acid-containing skeleton of the sphingofungin family of natural products. [ABSTRACT FROM AUTHOR] |
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| Database: |
Engineering Source |
