A two-step synthesis of the N-acylated a-azido-v-aminovalerate, a common intermediate for the synthesis of midpacamide and dispacamide, is described. This intermediate undergoes cyclization through the corresponding a-ureido ester derivative to give the 3-methylhydantoin ring present in midpacamide,
An efficient approach to dispacamide A and its derivatives
✍ Scribed by Guihéneuf, Solène ;Paquin, Ludovic ;Carreaux, François ;Durieu, Emilie ;Meijer, Laurent ;Bazureau, Jean Pierre
- Book ID
- 118152053
- Publisher
- Royal Society of Chemistry
- Year
- 2012
- Tongue
- English
- Weight
- 415 KB
- Volume
- 10
- Category
- Article
- ISSN
- 1477-0520
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We describe here a practical and efficient route to a homogeneous N-palmitoyl-D-erythro-sphingomyelin and its 13C-labeled derivatives. (2S,3R,4E)-2-Azido-3-(tert-butyldimethylsilyloxy)-4-octadecene-l-ol 1 was converted to the sphingosine equivalent 2 by treatment with triphenylphosphine and water. A