Total synthesis of cavicularin and riccardin C: addressing the synthesis of an arene that adopts a boat configuration.
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The synthesis, structure, and physical properties of macrocycles have fascinated chemists for many years. Their inherent properties make them useful in areas as diverse as ion transport across membranes, development of new antibiotics, and catalysis. In this Review, the authors examine the chemistry of macrocycles containing non-peptidic amino acid derived molecules; the analysis is discussed in terms of function, rather than structure or synthesis. It is revealed that the diverse and imaginative structures created by synthetic chemists are not being fully exploited in application-driven endeavors.
The construction of macrocycles by ring-closing metathesis (RCM) is often used as the key step in the synthesis of natural products containing large rings. This reaction is attractive because of its high functional group compatibility and the possibility for further transformations. The finding of suitable reaction conditions is critical for the success of the synthesis. In this Minireview we summarize the efforts of many research groups to develop efficient RCM reactions on their way towards the total synthesis of natural macrocyclic products. Their findings should help in future synthesis to reduce the time-consuming phase of the optimization of the reaction conditions.
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