Total Synthesis of (−)-Himgaline
Journal of the American Chemical Society2006Vol. 128(39), pp. 12654–12655
Citations Over TimeTop 15% of 2006 papers
Unmesh Shah, Samuel Chackalamannil, Ashit K. Ganguly, Mariappan V. Chelliah, Sergei Kolotuchin, Alexei V. Buevich, Andrew T. McPhail
Abstract
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.
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