The synthesis of -plicamine

The cleavage of various trifluoro acetate functionalised amines (e.g. see structures 16 and 19) has also been accomplished using base-catalysed hydrolysis with Ambersep 900 (OH- form) in methanol. Again, it was found expedient to heat these reactions under 

---

As an ultimate example of how polymer-supported reagents can be applied to alkaloid synthesis, their multiple applications in the synthesis of (+)-plicamine truly stands out (Scheme 18.17). In this synthesis, extensive use was made of parallel optimization methods in order to progress the forward route more rapidly. Again, microwave techniques worked especially well to achieve fast reaction times. The entire route, including optimization, was complete in just six weeks, without the need to rehearse the reactions using conventional solution-phase reagents or the requirement of separation methods. 

In the original article describing the synthesis of plicamine, extensive use was also made of the intermediate structures to deliver a range of new structural analogs for evaluation (Scheme 18.18). ... 

---