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Total Synthesis of (-)-Luminacin D
Julien Malassis1, Nathan Bartlett1, Kane Hands1
1Chemistry, University of Southampton , Highfield, Southampton SO17 1BJ, U.K.
Abstract:
A second-generation synthesis of (-)-luminacin D based on an early stage introduction of the trisubstituted epoxide group is reported, allowing access to the natural product in an improved yield and a reduced number of steps (5.4%, 17 steps vs 2.6%, 19 steps). A full account of the optimization work is provided, with the reversal of stereoselection in the formation of the C4 alcohol in equally excellent diastereoselectivity as the key improvement.
