Enantioselective Michael addition in the total synthesis of strychnos alkaloids

Synopsis

This talk will be delivered by Mr Adam Gammack of the University of Oxford.

To date, strychnine remains one of the most complex natural products of its size and to this day is still used in pest control. Its notorious toxicity in humans, with a lethal dose as small as 50 mg, has led to its use in murder and fictional killings from those of Alexander the Great to Agatha Christie characters.

Not all the Strychnos alkaloids are infamous poisons. Some recently isolated Strychnos alkaloids, have been shown to possess attractive biological profiles with significant bioactivity. Some syntheses of these alkaloids already exist but in order to secure sufficient quantities and fully determine the therapeutic potential of many of these Strychnos alkaloids, a new source of these target molecules is required.

A motif common to many alkaloids, is the 2-azabicyclo [3.3.1] nonane core (morphan), which is considered to be the most complex architecture to construct in strychnine. An intramolecular enamine-catalysed enantioselective Michael addition of achiral cyclohexanones to tethered conjugated esters using the novel catalyst creates morphan cores with three stereocentres in high enantioselectivity and almost perfect diastereoselectivity. 

The lecture will look at a few strategies for the effective synthesis of these alkaloids.

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