Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 6, Pages 2256-2261Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201912010
Keywords
amine synthesis; medicinal chemistry; total synthesis; photoredox chemistry; radical chemistry
Categories
Funding
- AstraZeneca
- Herchel Smith Scholarship Scheme
- EPSRC [EP/S020292/1]
- Royal Society
- EPSRC [EP/S020292/1] Funding Source: UKRI
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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.
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