254975-87-6Relevant academic research and scientific papers
Asymmetric synthesis of the northern segment of ephedradine C
Russell, Michael G.N.,Baker, Raymond,Ball, Richard G.,Thomas, Steven R.,Tsou, Nancy N.,Castro, Jose L.
, p. 893 - 899 (2000)
An asymmetric synthesis of the dihydrobenzofuran segment of ephedradine C has been achieved. Key steps include a chiral oxazolidinone-mediated aldol reaction to form a β-hydroxy ester, followed by a novel debenzylation and concomitant intramolecular cyclisation with iodotrimethylsilane. An asymmetric Michael reaction with a homochiral lithium amide was used to form the third and final chiral centre. The absolute stereochemistry of these three centres was confirmed by X-ray crystal-structure determinations.
