Plicamine total synthesis

Baxendale, I.R., Ley, S.V. and Piutti, C., Total Synthesis of the Amaryllidaceae Alkaloid (+)-plicamine and its unnatural enantiomer by using solid-supported reagents and scavengers in a multistep sequence of reactions, Angew. Chem., Int. Ed. Engl., 2002, 41, 2194. 

In fact, the Eey group reported the first total synthesis of (-i-)-plicamine 188 and its enantiomer using only a combination of supported reagents and scavengers to effect all of the synthetic steps. No less than thirteen immobilized systems were used to produce the clean product. Given the relative complexity of the molecule, the synthesis is a powerful demonstration of the ability to achieve multistep transformation without conventional chromatographic methods. 

Scheme 17 Total synthesis of Plicamine using solid-supported reagents by Ley et al.

The use of solid-supported reagents and scavengers in the synthesis of natural products has been eloquently demonstrated by Ley and colleagues in their total synthesis of (-l-)-plicamine 6, an amaryllidacea alkaloid, as well as the corresponding unnatural enantiomer (Scheme 3.4). " The same group made use of similar immobihzed reagents to synthesize libraries of nicotine derivatives. ... 

Baxendale IR, Ley SV, Piutti C. Total synthesis of the amar-yllidaceae alkaloid (-l-)-plicamine and its unnatural... 

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