Successive ring expansion (SuRE) in the synthesis of medium sized ring and macrocyclic libraries Zhongzhen Yang, Illya Zalessky, William P. Unsworth University of York, UK Medium sized rings (8 to 11-membered ring) and macrocycles (≥ 12-memered ring) are very important molecules in medicinal chemistry and many other scientific fields. Successive Ring Expansion (SuRE) has been developed in our group and proved to be an efficient method to synthesize medium sized and macrocyclic lactams and lactones. (Figure 1)
Figure 1. Successive Ring Expansion (SuRE) We applied the SuRE method to the synthesis of natural product (only three consecutive ring expansion steps can achieve the 15-membered Solomonamide macrocyclic core), developed novel methods to produce the medium sized and macrocyclic. Also, the ring expansion reaction of cyclophosphamides was studied, which performed pretty different to normal ring expansion reactions we did before). (Figure 2)
Figure 2. SuRE in the synthesis of natural product (Solomonamide macrocyclic core), sulfonamides, oxazophorines. In conclusion, we extended the application of SuRE method to the synthesis of natural product (Solomonamide macrocyclic core). And, different starting cyclic units and linkers were developed for SuRE, resulting to different ring expansion products (sulfonamides, oxazophorines) References 1. Z. Yang , C. R. B. Swanson and W. P. Unsworth, Synlett , 2022 , DOI:10.1055/a-1932-9717. 2. Z. Yang , I. Zalessky, R. G. Epton, A. C. Whitwood, J. M. Lynam and W. P. Unsworth, Angew. Chemie - Int. Ed. , DOI:10.1002/anie.202217178. 3. K. Y. Palate, Z. Yang , A. C. Whitwood and W. P. Unsworth, RSC Chem. Biol. , 2022, 3 , 334–340. 4. Zhongzhen Yang, Jerry Tam, Jack Wootton, Jason M Lynam and William P Unsworth, Counter-intuitive Ring Expansion reactions of P=O containing molecules (submitted to Chemical Communications )
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