153277-22-6Relevant academic research and scientific papers
Pummerer Synthesis of Chromanes Reveals a Competition between Cyclization and Reductive Chlorination
Acosta-Guzmán, Paola,Rodríguez-López, Alvaro,Gamba-Sánchez, Diego
supporting information, p. 6903 - 6908 (2019/09/30)
The competition between an unprecedented reductive chlorination and the Pummerer reaction was studied and applied to the synthesis of benzofused oxygen heterocycles including 3-aminochromanes and in the intramolecular chlorination of activated aromatic ri
Total synthesis of (-)-slaframine from (2R,3S)-3-hydroxyproline
Knight, David W.,Sibley, A. William
, p. 2179 - 2187 (2007/10/03)
The yeast reduction products (2R,3S)-N-Boc-3-hydroxyproline esters 23 have been converted into the 3-methoxymethoxyprolinal 26 which undergoes an efficient Julia olefination with the L-serine-derived amino sulfone 29. Selective reduction of the resulting alkene 31 using diimide and cyclization leads to N-(benzyloxycarbonyl)slaframine 33c and thence to natural (-)-slaframine 5 and its more stable, crystalline N-acetyl derivative 34.
