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- W1982606890 abstract "Complexity and the presence of stereogenic centers have been correlated with success as compounds transition from discovery through the clinic. Here we describe the synthesis of a library of pyran-containing macrocycles with a high degree of structural complexity and up to five stereogenic centers. A key feature of the design strategy was to use a modular synthetic route with three fragments that can be readily interchanged or shuffled to produce subtly different variants with distinct molecular shapes. A total of 352 macrocycles were synthesized ranging in size from 14- to 16-membered rings. In order to facilitate the generation of stereostructure-activity relationships, the complete matrix of stereoisomers was prepared for each macrocycle. Solid-phase assisted parallel solution-phase techniques were employed to allow for rapid analogue generation. An intramolecular nitrile-activated nucleophilic aromatic substitution reaction was used for the key macrocyclization step." @default.
- W1982606890 created "2016-06-24" @default.
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- W1982606890 date "2011-03-07" @default.
- W1982606890 modified "2023-10-16" @default.
- W1982606890 title "Fragment-based domain shuffling approach for the synthesis of pyran-based macrocycles" @default.
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- W1982606890 doi "https://doi.org/10.1073/pnas.1015255108" @default.
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