ArticleJournal of the American Chemical Society2026
Seven-Step Total Synthesis of Conidiogenone B Enabled by Radical Cyclizations.
Article in Journal of the American Chemical Society, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
We report herein a total synthesis of conidiogenone B, a complex cyclopiane diterpene exhibiting potent antibacterial activity against multidrug-resistant pathogens. Conidiogenone B and its natural congeners feature a congested 6/5/5/5 (A/B/C/D) tetracyclic carbon framework and multiple stereocenters, including four all-carbon quaternary centers. The challenge of conidiogenone total synthesis lies in how to efficiently construct the tetracyclic carbon framework, especially the A/B hydrindane moiety with two vicinal all-carbon quaternary centers at the ring junction. We developed an efficient strategy with a metal-hydride hydrogen atom transfer (MHAT)-initiated reductive olefin-nitrile radical cyclization to close the six-membered A ring and construct the angular methyl containing all-carbon quaternary center adjacent to an existing one, which was formed via a stereoselective Johnson-Claisen rearrangement. Two approaches were investigated to form the B ring. The first one involves a four-step sequence featuring an intramolecular aldol condensation to close the B ring. The second one-step approach utilizes a doubly activated cyclopropane derivative (1-(ethoxycarbonyl)cyclopropyl)triphenylphosphonium tetrafluoroborate as a formal 1,3-dipole in a one-pot stepwise (3 + 2) annulation, namely, α-alkylation followed by Wittig olefination, to construct the B ring. In addition, a MHAT-initiated Baran reductive olefin-enone cyclization (BROC) was employed to form the D ring, and a Stork-Danheiser alkylation transposition protocol was used to produce the BROC precursor. Overall, these enabling transformations delivered conidiogenone B in only 7 steps without using any protecting groups by maximizing C-C bond-forming events and minimizing individual functional group manipulation steps to achieve high efficiency and 100% ideality in terms of strategic step count.
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