ArticleJournal of the American Chemical Society2020
C-C Bond Cleavage Approach to Complex Terpenoids: Development of a Unified Total Synthesis of the Phomactins.
Article in Journal of the American Chemical Society, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed.
- Synthesis of diverse terpenoid frameworks via enzyme-enabled abiotic scaffold hop.Nature chemistry · 2025Article
- Skeletal Editing Strategies Driven by Total Synthesis.Accounts of chemical research · 2025Article
- Strategies and Tactics for Site Specific Deuterium Incorporation at Each Available Carbon Atom of α-Pinene.The Journal of organic chemistry · 2024Article
- Late-stage benzenoid-to-troponoid skeletal modification of the cephalotanes exemplified by the total synthesis of harringtonolide.Nature communications · 2024Article
- Natural Product Synthesis: The Endless Quest for Unreachable Perfection.ACS organic & inorganic Au · 2023Review
- Allylic hydroxylation of enones useful for the functionalization of relevant drugs and natural products.Nature communications · 2023Article
- Skeletal diversification by C-C cleavage to access bicyclic frameworks from a common tricyclooctane intermediate.Chemical communications (Cambridge, England) · 2023Article
- Catalytic Cross-Metathesis Reactions That AffordJournal of the American Chemical Society · 2023Article
- Development of a C-C Bond Cleavage/Vinylation/Mizoroki-Heck Cascade Reaction: Application to the Total Synthesis of 14- and 15-Hydroxypatchoulol.Journal of the American Chemical Society · 2022Article
- Strategy Evolution in a Skeletal Remodeling and C-H Functionalization-Based Synthesis of the Longiborneol Sesquiterpenoids.Journal of the American Chemical Society · 2022Article
- Site-selective amination and/or nitrilationChemical science · 2022Article
- Rearrangements of the Chrysanthenol Core: Application to a Formal Synthesis of Xishacorene B.Journal of the American Chemical Society · 2021Article
- Deconjugative α-Alkylation of Cyclohexenecarboxaldehydes: An Access to Diverse Terpenoids.The Journal of organic chemistry · 2021Article
- Deconstructive Asymmetric Total Synthesis of Morphine-Family Alkaloid (-)-Thebainone A.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
5 authors.
Funding
Abstract
The rearrangement of carbon-carbon (C-C) single bonds in readily available carbocyclic scaffolds can yield uniquely substituted carbocycles that would be challenging to construct otherwise. This is a powerful and often non-intuitive approach for complex molecule synthesis. The transition-metal-mediated cleavage of C-C bonds has the potential to broaden the scope of this type of skeletal remodeling by providing orthogonal selectivities compared to more traditional pericyclic and carbocation-based rearrangements. To highlight this emerging technology, a unified, asymmetric, total synthesis of the phomactin terpenoids was developed, enabled by the selective C-C bond cleavage of hydroxylated pinene derivatives obtained from carvone. In this full account, the challenges, solutions, and intricacies of Rh(I)-catalyzed cyclobutanol C-C cleavage in a complex molecule setting are described. In addition, details of the evolution of strategies that ultimately led to the total synthesis of phomactins A, K, P, R, and T, as well as the synthesis and structural reassignment of Sch 49027, are given.
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