Rapid Syntheses of (-)-FR901483 and (+)-TAN1251C Enabled by Complexity-Generating Photocatalytic Olefin Hydroaminoalkylation
| Autor: | Matthew J. Gaunt, Aaron Trowbridge, Dominik Reich |
|---|---|
| Přispěvatelé: | Gaunt, Matthew J [0000-0002-7214-608X], Apollo - University of Cambridge Repository |
| Rok vydání: | 2020 |
| Předmět: |
Olefin fiber
010405 organic chemistry Drug discovery Chemistry Total synthesis chemistry.chemical_element General Medicine General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry amine synthesis Catalysis 0104 chemical sciences medicinal chemistry Photocatalysis Amine synthesis radical chemistry total synthesis Carbon photoredox chemistry |
| Popis: | We report a common strategy to facilitate the syntheses of the polycyclic alkaloids (-)-FR901483 (1) and (+)-TAN1251C (2). A divergent synthetic strategy provides access to both natural products through a pivotal spirolactam intermediate (3), which can be accessed on a gram-scale. A photocatalytic olefin hydroaminoalkylation brings together three readily available building blocks and forges the majority of the carbon framework present in 1 and 2 in a single operation, leading to concise total syntheses. The complexity-generating photocatalytic process also provides direct access to novel non-racemic spirolactam scaffolds that are likely to be of interest to early-stage drug discovery programs. |
| Databáze: | OpenAIRE |
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