179469-45-5Relevant academic research and scientific papers
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.
Similarities and differences in the structure-activity relationships of capsaicin and resiniferatoxin analogues
Walpole, Christopher S. J.,Bevan, Stuart,Bloomfield, Graham,Breckenridge, Robin,James, Iain F.,Ritchie, Timothy,Szallasi, Arpad,Winter, Janet,Wrigglesworth, Roger
, p. 2939 - 2952 (2007/10/03)
Structure-activity relationships in analogues of the irritant natural product capsaicin have previously been rationalized by subdivision of the molecule into three structural regions (A, B, and C). The hypothesis that resiniferatoxin (RTX), which is a hig
