27 March 2014

Enantioselective Michael addition in the total synthesis of strychnos alkaloids

Organised by:

SCI's Thames and Kennet Regional Group

Charterhouse School, Godalming

Registration Closed

This event is no longer available for registration.

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.


Venue and Contact

Charterhouse

Room 105, Charterhouse School, 
Charterhouse, Godalming, GU7 2DX 

 

Oliver Choroba

Tel: 01483 291713

Email: owc@charterhouse.org.uk


Fees

This is a FREE event - early booking is advised

Become an SCI Member and save on this and future events

See Membership Options

Sign up as an Event Member to join this event. SCI Full or Student Members receive discounts on event registrations