期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 17, 期 36, 页码 9957-9969出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201100425
关键词
asymmetric catalysis; diterpene; natural product; palladium; total synthesis
资金
- 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
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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