Construction of an asymmetric quaternary carbon via an asymmetric aza-Claisen rearrangement and its application in the total synthesis of (+)-α-cuparenone |
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| Authors: | Takeshi Nishii Fumiaki Miyamae Makoto Yoshizuka Hiroto Kaku Mitsuyo Horikawa Makoto Inai Tetsuto Tsunoda |
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| Institution: | Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Tokushima 770-8514, Japan |
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| Abstract: | Excess lithium hexamethyldisilazide (LHMDS) with LiCl prompted the asymmetric aza-Claisen rearrangement of carboxamide and retarded the decomposition of its amide enolate. The addition of these two reagents was a key step that led to the total synthesis of (+)-α-cuparenone with a stereogenic quaternary center. |
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