161644-41-3Relevant academic research and scientific papers
SYNTHESIS OF A SIMPLE KAINIC ACID ANALOGUE BY MEANS OF CARBAMOYLMETHYL RADICAL CYCLIZATION
Sato, Tatsunori,Matsubayashi, Ken-ichiro,Yamamoto, Kazumi,Ishikawa, Hiroko,Ishibashi, Hiroyuki,Ikeda, Masazumi
, p. 261 - 270 (2007/10/02)
A new approach to (-)-(2S,3R)-2-carboxy-3-pyrrolidineacetic acid (6) starting from D-serine is described.The key step is a radical cyclization of tert-butyl (S)-3-oxazolidin-4-yl>-(E)-propenoate (15b), which gave tert-butyl (6S,7R,7aS)-5,6,7,7a-tetrahydro-3,3-dimethyl-5-oxo-6-phenylthio-1H,3H-pyrrolooxazol-7-ylacetate (16b) in a highly regio- and diastereo-selective manner.The compound (16b) was then coverted into tert-butyl (4R,5S)-5-(tert-butyldimethylsilyloxymethyl)-1-methoxycarbonyl-2-oxopyrrolidin-4-ylacetate (19) by standard chemical manipulations, which has already been transformed to 6.
