Abstract
The stunning advances in understanding the reactivity and selectivity principles of asymmetric pericyclic reactions have had a profound impact on the synthetic planning of complex natural products. Indeed, electrocyclizations, cycloadditions, and sigmatropic rearrangements enable synthetic chemists to craft highly functionalized scaffolds that would not otherwise be possible with a similar atom-, step-, and redox-economy. In this review, selected examples from the last two decades of research (2003–2020) on tandem processes combining oxa-6π electrocyclic reactions are discussed in terms of reactivity challenges, inherent reversibility, and key structural bond formation in the assembly of natural products. A particular emphasis is given to the electrocyclic ring-closures in the tandem processes featuring Knoevenagel-type condensations, Diels–Alder cycloadditions, Stille couplings, and oxidative dearomatizations. The synthetic manifolds reviewed here illustrate how oxa-6π electrocyclizations are intimately linked to the construction of complex natural product scaffolds and have inspired a number of biomimetic syntheses in the laboratory.
Highlights
Natural products have long held societal value as folk medicines, and even in this modern era, many FDA-approved drugs are still being derived from terpenes and alkaloids found in nature
Pericyclic reactions [1] presented in this special issue of Organics are some of the most powerful manifolds to streamline the construction of complex polycyclic natural products
2H-pyrans related 2H-benzopyrans arescaffolds privileged scaffolds found in natural products attracted the interests of synthetic chemists for decades
Summary
Natural products have long held societal value as folk medicines, and even in this modern era, many FDA-approved drugs are still being derived from terpenes and alkaloids found in nature. From a fundamental stand-point, the total synthesis of natural products remains one of the most exhilarating areas of chemical research by providing a unique platform for the discovery of novel technologies, methodologies, and synthetic strategies to provide a more sustainable and reliable access to biologically active molecules. In this context, pericyclic reactions [1] presented in this special issue of Organics (e.g., electrocyclizations [2,3], cycloadditions [4], and sigmatropic rearrangements [5]) are some of the most powerful manifolds to streamline the construction of complex polycyclic natural products.
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