Journal
ORGANIC LETTERS
Volume 20, Issue 18, Pages 5784-5788Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.8b02478
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Funding
- Agencia Estatal de Investigation (MINECO/AEI/FEDER, UE) [CTQ2016-75960-P]
- AEI-Severo Ochoa Excellence Accreditation [SEV-2013-0319]
- MEC (FPU fellowship)
- European Research Council [321066]
- AGAUR [2017 SGR 1257]
- CERCA Program/Generalitat de Catalunya
- ICIQ Foundation
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The first total synthesis of repraesentin F has been accomplished by a highly diastereoselective gold(I)-catalyzed cyclization cascade as the key step. This cycloisomerization/Prins-type tandem transformation enabled direct access to the atypical tricyclic carbon skeleton of the natural product with the required syn/anti/syn ring fusion. This synthetic effort also allowed reassignment of the relative configuration of repraesentin F and determination of its absolute configuration.
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