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3.2.3.1.1.1 Wittig-Based Macrocyclization in DNA-Templated Libraries

DOI: 10.1055/sos-SD-241-00235

Gillingham, D.; Sauter, B.Science of Synthesis: DNA-Encoded Libraries, (20241562.

An early example of macrocyclization in DNA-encoded chemistry is found in the pioneering DNA-templated synthesis work of the Liu group.[‌6‌‌8‌] They built a series of DNA-linked reagents that could then be selectively reacted with a growing small molecule attached to the end of a template DNA. In the penultimate step of their synthesis, they introduced (through amide coupling) a small library of phosphonium salts capable of producing stabilized phosphorus ylides at high pH. By oxidatively cleaving a diol on the other end of the molecule with periodate and then raising the pH, they initiated an intramolecular Wittig reaction to form the macrocycle.[‌6‌] Although, in general, the DNA-templated library design used by the Liu group has been superseded by the DNA-recorded chemistry championed by Praecis[‌9‌] and the ETH DEL lab,[‌10‌,‌11‌] it is strange that Wittig chemistry has not since been used in DEL synthesis, as the reaction is highly efficient, delivering 60–90% yield across 11 individual substrates tested.

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