Document Type
Article
Version
Author's Final Manuscript
Publication Title
Organic and Biomolecular Chemistry
Volume
13
Publication Date
2015
Abstract
Due to the profound extent to which natural products inspire medicinal chemists in drug discovery, there is demand for innovative syntheses of these often complex materials. This article describes the synthesis of tricarbocyclic natural product architectures through an extension of the enantioselective Birch-Cope sequence with intramolecular Friedel-Crafts alkylation reactions. Additionally, palladium-catalyzed enol silane cycloalkenylation of the tricarbocyclic structures afforded the challenging bicyclo[3.2.1]octane C/D ring system found in the gibberellins and the ent-kauranes, two natural products with diverse medicinal value. In the case of the ent-kaurane derivative, an unprecedented alkene rearrangement converted four alkene isomers to one final product.
Publisher's Statement
Original published version available here: http://www.ncbi.nlm.nih.gov/pubmed/25598198
Citation
“The Enantioselective Construction of Tetracyclic Diterpene Skeletons with Friedel-Crafts Alkylation and Palladium-catalyzed Cycloalkenylation Reactions” Sarah J. Burke, William P. Malachowski, Sharan K. Mehta and Roselyn Appenteng. Organic & Biomolecular Chemistry 2015, 13, 2726-2744.
DOI
10.1039/c4ob02489c