479-39-0Relevant articles and documents
FUMARIACEAE ALKALOIDS INCLUDING THE BIOGENETIC PRECURSOR OF CULARINE
Blaschke, Gottfried,Scriba, Gerhard
, p. 585 - 588 (1985)
Key Word Index - Corydalis claviculata; Fumariaceae;benzylisoquinoline alkaloids; cularines; (+)-crassifoline; (+)-sarcocapnidine; (+)-claviculine; (+)-O-methylcularicine. - Corydalis claviculata has yielded (+)-crassifoline, the first 7,8,3',4'-oxygenated benzylisoquinoline and biogenetic precursor of cularine, as well as the new cularine alkaloids (+)-sarcocapnidine, (+)-claviculine and (+)-O-methylcularicine.
Diastereoselective Synthesis of Cularine Alkaloids via Enium Ions and an Easy Entry to Isoquinolines by Aza-Wittig Electrocyclic Ring Closure
Rodrigues, J. Augusto R.,Abramovitch, Rudolph A.,De Sousa, Joana D. F.,Leiva, Genaro C.
, p. 2920 - 2928 (2007/10/03)
In preliminary communications, we reported the diastereoselective synthesis of cularine and sarcocapnine via the intramolecular ring closure of nitrenium and oxenium ions, a new highly diastereoselective reductive methylation with (+)-8-phenylmenthyl chloroacetate followed by reduction with sodium borohydride, and a facile entry to the isoquinoline precursors by aza-Wittig electrocyclic ring closure. We now report the full details of the syntheses of (+)-O-demethylcularine, (+)-cularine, (+)-sarcocapnidine, (+)-sarcocapnine, and (+)-crassifoline and describe different methods of synthesis of their precursors.
