274675-75-1Relevant academic research and scientific papers
Total syntheses of (±) and (-)-stemoamide
Jacobi, Peter A.,Lee, Kyungae
, p. 4295 - 4303 (2000)
(±)-Stemoamide (1) was prepared in seven steps beginning with y- chlorobutryl chloride (20) and succinimide (15), which were efficiently converted to the key alkyne oxazole 17 on a multigram scale. Intramolecular (Diels-Alder)-(retro-Diels-Alder) reaction of 17 then gave butenolide 12b directly upon aqueous workup. The remaining two stereocenters in 1 were established in a single step by a highly selective reduction of 12b (NaBH4/NiCl2), followed by equilibration to the thermodynamically favored natural configuration. In analogous fashion (-)-stemoamide (1) was prepared beginning with L-pyroglutamic acid (S-35).
