Recent advances in thetotal synthesisofnatural productscontaining eight-membered carbocycles (2009–2019)

Abstract Click to copy section link Section link copied! Natural products containing eight-membered carbocycles constitute a class of structurally intriguing and biologically important molecules such as the famous diterpenes taxol and vinigrol. Such natural products are being increasingly investigated because of their fascinating architectural features and potent medicinal properties. However, synthesis of natural products with cyclooctane moieties has proved to be highly challenging.

This review highlights the recently completed total syntheses of natural products with eight-membered carbocycles with a focus on strategic considerations. A collection of 27 representative studies from the literature covering the decade from 2009 to 2019 is described in chronological order with relevant studies grouped together, including syntheses of the same natural product by different research groups using different strategies. Finally, a summary and outlook including a discussion of the major features of each strategy used in the syntheses are presented. This review illustrates the diversity and creativity in the elegant synthetic designs of eight-membered carbocycles.

We hope this review will provide timely illumination and beneficial guidance for future synthetic efforts for organic chemists who are interested in this area. ACS Publications Copyright © 2020 American Chemical Society Subjects what are subjects Article subjects are automatically applied from the ACS Subject Taxonomy and describe the scientific concepts and themes of the article. Chemical synthesis Cyclization Ketones Organic synthesis Pharmaceuticals