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Total Synthesis of the Tetracyclic Lupin Alkaloid (+)-Allomatrine

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journal contribution
posted on 06.09.2013, 00:00 by Samuel V. Watkin, Nicholas P. Camp, Richard C. D. Brown
(+)-Allomatrine (1) has been synthesized using an imino-aldol reaction and N-acyliminium cyclization as key steps. Strategically, use of the tert-butylsulfinimine derivative of (E)-4-(trimethylsilyl)but-2-enal enabled the staged formation of three C–C bonds, a C–N bond, and the four stereogenic centers within the target.