913832-80-1Relevant articles and documents
Total synthesis of (-)-himgaline
Shah, Unmesh,Chackalamannil, Samuel,Ganguly, Ashit K.,Chelliah, Mariappan,Kolotuchin, Sergei,Buevich, Alexei,McPhail, Andrew
, p. 12654 - 12655 (2008/02/05)
The first total synthesis of (-)-himgaline and a highly enantioselective synthesis of its congener (-)-GB 13 are described. Decarboxylative aza-Michael reaction of the hexacyclic lactone precursor under acidic conditions, followed by basic workup, yielded (-)-GB 13 in 80% yield. Cyclization of (-)-GB 13 to oxohimgaline under acidic conditions, followed by internally coordinated sodium triacetoxyborohydride reduction, gave (-)-himgaline as the exclusive product. Copyright