(-)-Bipolarolide D is an ophiobolin-derived sesteterpenoid with a unique tetraquinane (5/5/5/5) tetracyclic skeleton decorated with a diverse set of functionalities. Herein we report a robust, scalable, and efficient total synthesis of this natural product in 1.8% overall yield. The developed approach features a diastereoselective Pauson-Khand reaction, a highly efficient Rautenstrauch cycloisomerization, and radical cyclization to forge the carbon backbone and the installation of the side chain via crotylation with 1-methyl-2-propenylmagnesium chloride followed by Suzuki cross-coupling.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11600160 | PMC |
| http://dx.doi.org/10.1021/jacsau.4c00680 | DOI Listing |
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