Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 17, Issue 36, Pages 9957-9969Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201100425
Keywords
asymmetric catalysis; diterpene; natural product; palladium; total synthesis
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Funding
- King Abdullah University of Science and Technology (KAUST) [KUS-11-006-02]
- NIH-NIGMS [R01M080269-01]
- Amgen
- Abbott
- Boehringer Ingelheim
- Merck
- Bristol-Myers Squibbs
- GlaxoSmithKline
- Johnson and Johnson
- Merck Research Laboratories
- Pfizer
- Novartis
- Roche
- Abbott Laboratories
- AstraZeneca
- Caltech
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A concise and versatile approach toward the preparation of the cyanthiwigin family of cyathane natural products is described. By leveraging a unique double asymmetric catalytic alkylation procedure it is possible to quickly establish two of the most critical stereocenters of the cyanthiwigin framework with high levels of selectivity and expediency. The synthetic route additionally employs both a tandem ring-closing cross-metathesis reaction, and an aldehyde-olefin radical cyclization process, in order to rapidly arrive at the tricyclic cyathane core of the cyanthiwigin molecules. From this unifying intermediate, the preparations of cyanthiwigins B, F, and G are attained swiftly and without the need for protecting groups.
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