16625-34-6Relevant articles and documents
Synthetic studies toward galbulimima alkaloid (-)-GB 13 and (+)-GB 16 and (-)-himgaline
Zi, Weiwei,Yu, Shouyun,Ma, Dawei
, p. 573 - 579 (2011/10/03)
Condensation of (S)-3-aminobutan-1-ol with 1,3-cyclohexane-dione followed by an intramolecular alkylation afforded bicyclic enamine 32, which was converted into enone 35 through a diastereoselective hydrogenation. Mukaiyama-Michael addition of a bicyclic
Total synthesis of (+)-galbulimima alkaloid 13 and (+)-himgaline
Evans, David A.,Adams, Drew J.
, p. 1048 - 1049 (2007/10/03)
The stereoselective syntheses of (+)-himgaline (1) and (+)-GB13 (2) are described. Important diastereoselective bond constructions include an intramolecular Diels-Alder reaction, an intramolecular Michael addition, and an intramolecular enamine aldol addi
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
