Efficient total synthesis of (-)-stemoamide.
An efficient diastereoselective synthesis of (-)-stemoamide has been accomplished from a pyroglutamic acid derivative in eight steps and with 24% overall yield. The synthesis features an intramolecular samarium diiodide-promoted 7-exo-trig cyclization of a ketyl radical generated from the corresponding aldehyde.
Faculty of Pharmaceutical Sciences, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan. honda@hoshi.ac.jp
Toshio
T
Honda
Tomoha
T
Matsukawa
Kazunori
K
Takahashi
D003500:Cyclization; D005609:Free Radicals / Q000737:chemistry; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
D005609:Free Radicals; D006575:Heterocyclic Compounds, 3-Ring; D007783:Lactones; C519217:stemoamide