title: Total syntheses of cyanthiwigins B, F, and G.
abstract: 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.
authors.affiliation: The Arnold and Mable Beckman Laboratories of Chemical Synthesis Department of Chemistry and Chemical Engineering, California Institute of Technology, 1200 East California Blvd., MC 101-20, Pasadena, CA 91125, USA.
authors.forename: John A
authors.initials: JA
authors.lastname: Enquist
authors.forename: Scott C
authors.initials: SC
authors.lastname: Virgil
authors.forename: Brian M
authors.initials: BM
authors.lastname: Stoltz
mesh_terms: D045744:Cell Line, Tumor; D004224:Diterpenes / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D020932:Nerve Growth Factor / Q000096:biosynthesis
chemical_list: D004224:Diterpenes; C511567:cyanthiwigin B; C530546:cyanthiwigin F; C568709:cyanthiwigin G; D020932:Nerve Growth Factor