Facile generation of bridged medium-sized polycyclic systems by rhodium-catalysed intramolecular (3+2) dipolar cycloadditions

Bao-Long Hou, Jonathan J. Wong, Na Lv, Yong-Qiang Wang, K. N. Houk () and Chuang-Chuang Li ()
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Bao-Long Hou: Southern University of Science and Technology
Jonathan J. Wong: University of California, Los Angeles
Na Lv: Southern University of Science and Technology
Yong-Qiang Wang: Southern University of Science and Technology
K. N. Houk: University of California, Los Angeles
Chuang-Chuang Li: Southern University of Science and Technology

Nature Communications, 2021, vol. 12, issue 1, 1-8

Abstract: Abstract Bridged medium-sized bicyclo[m.n.2] ring systems are common in natural products and potent pharmaceuticals, and pose a great synthetic challenge. Chemistry for making bicyclo[m.n.2] ring systems remains underdeveloped. Currently, there are no general reactions available for the single-step synthesis of various bridged bicyclo[m.n.2] ring systems from acyclic precursors. Here, we report an unusual type II intramolecular (3+2) dipolar cycloaddition strategy for the syntheses of various bridged bicyclo[m.n.2] ring systems. This rhodium-catalysed cascade reaction provides a relatively general strategy for the direct and efficient regioselective and diastereoselective synthesis of highly functionalized and synthetically challenging bridged medium-sized polycyclic systems. Asymmetric total synthesis of nakafuran-8 was accomplished using this method as a key step. Quantum mechanical calculations demonstrate the mechanism of this transformation and the origins of its multiple selectivities. This reaction will inspire the design of the strategies to make complex bioactive molecules with bridged medium-sized polycyclic systems.

Date: 2021
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DOI: 10.1038/s41467-021-25513-7

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