Macrocyclic natural products

Meng, Q., Hesse, M. Ring Closure Methods in the Synthesis of Macrocyclic Natural Products. 161, 107-176 (1991). 

Keywords Macrocycles Natural products Diversity-oriented synthesis ... 

Total synthesis of complex (macrocyclic) natural products using fast and flexible strategies and diversity-oriented synthesis of natural product-like macrocycles are important research topics in our laboratory. The following sections describe the total synthesis of epothilone D and epothilone D5 analogues, DOS of cyclopeptide alkaloid analogues, of biaryl ether macrocycles, and of steroid/peptide hybrid macrocycles, respectively. 

The transition metal catalyzed synthesis of seven membered and larger heterocycles attracted considerably less attention than the preparation of their five and six membered analogues. Typical examples in this chapter include the formation of heterocycles in insertion reactions, or through carbon-heteroatom bond formation. Although the formation of some macrocyclic natural products was also achieved in cross-coupling reactions they will not be discussed in detail. 

The formation of seven membered heterocycles and larger rings through cross-coupling reactions is quite rare (except for some macrocyclic natural products). An example of such a process is presented in 5.1. The intramolecular Stille-coupling of the tributylstannyl-indole and vinyl bromide moieties led to the formation of a seven membered ring in good yield.1... 

We sorely need new and improved anticancer drugs. Much excitement has been generated by the development of taxol (78), a macrocyclic natural product with a novel mechanism, the stabilization of microtubules (Suffness,... 

The Stork-Takahashi method has been applied to the synthesis of a number of macrocyclic natural products including Muscone,217 Sarcophytol-A2H and Peri-planone B.220... 

Ring Closure Methods in the Synthesis of Macrocyclic Natural Products... 

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