[ { "id": "authors:a4fa0-tnp50", "collection": "authors", "collection_id": "a4fa0-tnp50", "cite_using_url": "https://authors.library.caltech.edu/records/a4fa0-tnp50", "type": "article", "title": "Enantioselective Synthesis of (+)-Auriculatol A", "author": [ { "family_name": "Thompson", "given_name": "Jordan K.", "orcid": "0009-0007-6395-7087", "clpid": "Thompson-Jordan-Kenji" }, { "family_name": "Youngblood", "given_name": "Kala C.", "orcid": "0000-0002-4686-1979", "clpid": "Youngblood-Kala-C" }, { "family_name": "Teh", "given_name": "Yun Hao Shawn", "orcid": "0009-0005-4981-7841", "clpid": "Teh-Yun-Hao-Shawn" }, { "family_name": "Farley", "given_name": "Conner M.", "orcid": "0000-0002-4067-0848", "clpid": "Farley-Conner-M" }, { "family_name": "Zhang", "given_name": "Zhehao", "orcid": "0009-0008-7893-1274", "clpid": "Zhang-Zhehao" }, { "family_name": "Virgil", "given_name": "Scott C.", "orcid": "0000-0001-8586-5641", "clpid": "VIrgil-S-C" }, { "family_name": "Reisman", "given_name": "Sarah E.", "orcid": "0000-0001-8244-9300", "clpid": "Reisman-S-E" } ], "abstract": "A total synthesis of the grayanane diterpenoid (+)-auriculatol A is reported. The synthesis features a convergent coupling strategy that joins two fragments by a vinylogous Mukaiyama-aldol-type reaction and then constructs the 7-membered ring by a Ni-catalyzed enolate alkenylation. Key findings include the development of a chemoselective Ni-catalyzed intramolecular 1,2-addition to access the bicyclo[3.2.1]octane fragment and the use of electron-deficient olefin supporting ligands as uniquely effective for the Ni-catalyzed enolate alkenylation.", "doi": "10.1021/jacs.5c17269", "pmcid": "PMC12636016", "issn": "0002-7863", "publisher": "American Chemical Society", "publication": "Journal of the American Chemical Society", "publication_date": "2025-11-19", "series_number": "46", "volume": "147", "issue": "46", "pages": "42170\u201342174" }, { "id": "authors:5nayq-z0k75", "collection": "authors", "collection_id": "5nayq-z0k75", "cite_using_url": "https://authors.library.caltech.edu/records/5nayq-z0k75", "type": "monograph", "title": "Radical stabilization in organic flow batteries enabled by chirality", "author": [ { "family_name": "Carrington", "given_name": "Mark", "orcid": "0009-0007-5464-0889" }, { "family_name": "Miller", "given_name": "Kirya" }, { "family_name": "Tkachenko", "given_name": "Nikolay" }, { "family_name": "Clark", "given_name": "Ainsley" }, { "family_name": "Rao", "given_name": "Guodong" }, { "family_name": "Chung", "given_name": "H.T. Katie" }, { "family_name": "Virgil", "given_name": "Scott", "orcid": "0000-0001-8586-5641", "clpid": "VIrgil-S-C" }, { "family_name": "Tao", "given_name": "Alice" }, { "family_name": "Lem", "given_name": "Xavier" }, { "family_name": "Smith", "given_name": "Patrick" }, { "family_name": "Settineri", "given_name": "Nicholas" }, { "family_name": "Helms", "given_name": "Brett" }, { "family_name": "Britt", "given_name": "R. David" }, { "family_name": "Head-Gordon", "given_name": "Martin" }, { "family_name": "Toste", "given_name": "F. Dean" } ], "abstract": "The practical realization of organic redox flow batteries (RFBs) for grid-scale energy storage is limited by complex active material degradation pathways frequently featuring one or more free radical species. Here we develop strategies for stabilization of mono- and di-radicals in organic 2e- electrolytes. Leveraging steric differences between isomers of cyclic triindole catholytes, we show that capacity fade arising from radical-based processes can be controlled by adjusting the chirality, intramolecular chiral induction, and degree of out of plane torsion \u2013 all without influencing redox potential. We further show that diradical decomposition follows at least two pathways, the preference for which can be biased using chirality, suggesting the presence of a chirality induced spin selectivity (CISS) effect. Once stabilized, triindole radicals can be co-formulated directly with viologen based electrolytes in 2e- symmetric, membraneless and all-organic full-cell configurations with little fade, air-tolerance, > 75% energy efficiency, robust self-discharge resistance and plausible pathways for large scale production.", "doi": "10.26434/chemrxiv-2025-vbw2s", "publisher": "ChemRxiv", "publication_date": "2025-10-15" }, { "id": "authors:sc9kv-n4b93", "collection": "authors", "collection_id": "sc9kv-n4b93", "cite_using_url": "https://authors.library.caltech.edu/records/sc9kv-n4b93", "type": "monograph", "title": "Divergent Total Syntheses of Pyrroloiminoquinone Alkaloids Enabled by the Development of a Larock/Buchwald\u2013Hartwig Annulation/Cyclization", "author": [ { "family_name": "Rezgui", "given_name": "Samir", "orcid": "0000-0003-4080-9835", "clpid": "Rezgui-Samir" }, { "family_name": "Farhi", "given_name": "Jonathan", "clpid": "Farhi-Jonathan" }, { "family_name": "Yu", "given_name": "Hao", "orcid": "0009-0008-6002-6276", "clpid": "Yu-Hao" }, { "family_name": "Sercel", "given_name": "Zachary", "orcid": "0000-0001-7977-8509", "clpid": "Sercel-Zachary" }, { "family_name": "Virgil", "given_name": "Scott", "orcid": "0000-0001-8586-5641", "clpid": "VIrgil-S-C" }, { "family_name": "Stoltz", "given_name": "Brian M.", "orcid": "0000-0001-9837-1528", "clpid": "Stoltz-B-M" } ], "abstract": "

Pyrroloiminoquinone alkaloids are a large class of natural products that display a wide range of biologi-cal activities. Synthetic approaches to these natural products typically rely on a common late-stage C10-oxygenated pyrroloiminoquinone intermediate, but these strategies often lead to lengthy synthetic sequences that are not ame-nable to divergent syntheses. We devised an alternative approach aimed at the early introduction of the C10 nitro-gen, which we hypothesized would enable late-stage diversification. This strategy hinged upon a Larock/Buchwald–Hartwig annulation/cyclization to quickly access the core of these alkaloids. We report the development of this cas-cade process, which was facilitated by a dual ligand system in addition to selective functionalization of the key inter-mediate, to provide the shortest total syntheses to date of makaluvamines A, C, and D and isobatzelline B, and the first total synthesis of makaluvamine N.

", "doi": "10.26434/chemrxiv-2024-9jmfb", "publisher": "ChemRxiv", "publication_date": "2024-02-16" } ]