AI Article Synopsis
- - The rearrangement of carbon-carbon (C-C) single bonds in carbocyclic compounds allows for the creation of uniquely modified structures, making it easier to synthesize complex molecules.
- - Transition-metal-mediated C-C bond cleavage offers new methods for modifying these structures, providing selectivity advantages over traditional rearrangement techniques.
- - The document details a successful total synthesis of phomactin terpenoids, showcasing the use of selective C-C bond cleavage in creating complex molecules and discussing challenges and strategies involved in this process.
Article 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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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7771649 | PMC |
| http://dx.doi.org/10.1021/jacs.0c07316 | DOI Listing |
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