KAUST Grant NumberKUS-11-006-02
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AbstractA 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.
CitationEnquist JA, Virgil SC, Stoltz BM (2011) Total Syntheses of Cyanthiwigins B, F, and G. Chem Eur J 17: 9957–9969. Available: http://dx.doi.org/10.1002/chem.201100425.
SponsorsThis publication is based on work supported by Award No. KUS-11-006-02, made by King Abdullah University of Science and Technology (KAUST). The authors wish to thank NIH-NIGMS (R01M080269-01), Amgen, Abbott, Boehringer Ingelheim, Merck, and Bristol-Myers Squibbs, GlaxoSmithKline, Johnson and Johnson, Amgen, Merck Research Laboratories, Pfizer, Novartis, Roche, Abbott Laboratories, Boehringer-Ingelheim, AstraZeneca, and Caltech for financial support. We also wish to thank Dr. M. W. Day and Mr. L. M. Henling for X-ray crystallographic expertise, Dr. Andrew Harned, Dr. David White, Daniel Caspi, and J. T. Mohr for helpful discussions, and Professor Mark T. Hamann for authentic samples and spectra of cyanthiwigins B, F, and G. Ruthenium olefin metathesis catalysts were generously donated by Materia.
JournalChemistry - A European Journal
PubMed Central IDPMC3365662
CollectionsPublications Acknowledging KAUST Support
- Total synthesis of cyanthiwigins A, C, G, and H.
- Authors: Wang C, Wang D, Gao S
- Issue date: 2013 Sep 6
- Asymmetric synthesis of the tricyclic core of NGF-inducing cyathane diterpenes via a transition-metal-catalyzed [5 + 2] cycloaddition.
- Authors: Wender PA, Bi FC, Brodney MA, Gosselin F
- Issue date: 2001 Jun 28
- The total synthesis of (-)-cyanthiwigin F by means of double catalytic enantioselective alkylation.
- Authors: Enquist JA Jr, Stoltz BM
- Issue date: 2008 Jun 26
- Total synthesis of (+)-cyanthiwigin U.
- Authors: Pfeiffer MW, Phillips AJ
- Issue date: 2005 Apr 20
- Enantioselective total synthesis of briarellins E and F: the first total syntheses of briarellin diterpenes.
- Authors: Corminboeuf O, Overman LE, Pennington LD
- Issue date: 2003 Jun 4