Rapid Syntheses of (-)-FR901483 and (+)-TAN1251C Enabled by Complexity-Generating Photocatalytic Olefin Hydroaminoalkylation.
Angewandte Chemie (International ed. in English)
John Wiley & Sons Ltd.
MetadataShow full item record
Reich, D., Trowbridge, A., & Gaunt, M. (2020). Rapid Syntheses of (-)-FR901483 and (+)-TAN1251C Enabled by Complexity-Generating Photocatalytic Olefin Hydroaminoalkylation.. Angewandte Chemie (International ed. in English), 59 (6), 2256-2261. https://doi.org/10.1002/anie.201912010
We report a common strategy to facilitate the syntheses of the polycyclic alkaloids (−)-FR901483 (1) and (+)-TAN1251C (2). A divergent synthetic strategy provides access 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.
AstraZeneca, Herchel Smith Scholarship Scheme, EPSRC (EP/S020292/1), Royal Society
Royal Society (wm140104)
External DOI: https://doi.org/10.1002/anie.201912010
This record's URL: https://www.repository.cam.ac.uk/handle/1810/298748
All rights reserved