Biomimetric synthesis

Mechanistic studies are an important tool to understand how the biosynthesis of natural products occurs in nature and how to mimic their synthesis in the laboratory. Progress in this field includes the biomimetric synthesis of flavonolignan diastereomers in milk thistle (13JOC7594) and the chemoenzymatic synthesis of tetrahydropyran-containing polyketides (13AGE13215). In the synthetic domain, DFT calculations and experimental assays have been carried out to explain the multiple mechanisms involved in the palladium(II)-catalyzed Sn2 reactions of aUylic alcohols to prepare chiral tetrahydropyran derivatives (13JOC7664). 

Schwartz and Shanzer have used silicon as a metaloid template for the one-step synthesis of biomimetric macrocycles (Lifson et al., 1987). Silicon functions as a covalent template by forming weak bonds to the heteroatoms and can be easily removed using mild cpnditions. Silicon tetraisocyanate was reacted with ethylene glycol followed by carbonyl diimidazole to give a polycyclic product that was desiliconated with water. 

Tatsuta K, Misawa H, Chikauchi K. Biomimetric total synthesis of quinolactacin B, TNF production inhibitor, and its analogs. J. Antibiot. 2001 54(1) 109-112. 

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