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An Efficient Enantioselective Synthesis of (2 R )-Hydroxymethyl Glutamic Acid and an Approach to the (2 R )-Hydroxymethyl-Substituted Sphingofungins

✍ Scribed by Hayes, Christopher J.; Bradley, Daniel M.; Thomson, Nicholas M.


Book ID
126267367
Publisher
American Chemical Society
Year
2006
Tongue
English
Weight
108 KB
Volume
71
Category
Article
ISSN
0022-3263

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An efficient enantioselective synthesis
✍ A.I. Meyers; Thomas J. Sowin; Stefan Scholz; Yasutsugu Ueda πŸ“‚ Article πŸ“… 1987 πŸ› Elsevier Science 🌐 French βš– 215 KB

Cycloaddition of the enantiomeric 4-acetoxy-2-azetidinone (5) with the 2-siloxy-1,3butadiene (8) gives the carbacephem 9 which is cleaved via ozone and cyclized to the carbapenem system (+)-13 in 30% overall yield. The extensive activity directed toward the carbapenem systems (1, 2) due to their hig