Work

Total Syntheses of Cyanthiwigins B, F, and G

Year: 2011

Type: article

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.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.201100425

Authors: John A. Enquist, Scott C. Virgil, Brian M. Stoltz

Institution: California Institute of Technology

Language: English

Topic: Organic Chemistry Synthesis Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: U.S. Public Health Service, National Institute of General Medical Sciences

Awards: G1804838697, The Synthesis of Bioactive Polycyclic Natural Products