Ti(Oi-Pr)4-promoted photoenolization Diels–Alder reaction to construct polycyclic rings and its synthetic applications

Baochao Yang, Kuaikuai Lin, Yingbo Shi and Shuanhu Gao ()
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Baochao Yang: East China Normal University
Kuaikuai Lin: East China Normal University
Yingbo Shi: East China Normal University
Shuanhu Gao: East China Normal University

Nature Communications, 2017, vol. 8, issue 1, 1-10

Abstract: Stereoselective construction of polycyclic rings with all-carbon quaternary centers, and vicinal all-carbon quaternary stereocenters, remains a significant challenge in organic synthesis. These structures can be found in a wide range of polycyclic natural products and drug molecules. Here we report a Ti(Oi-Pr)4-promoted photoenolization/Diels–Alder (PEDA) reaction to construct hydroanthracenol and related polycyclic rings bearing all-carbon quaternary centers. This photolysis proceeds under mild conditions and generates a variety of photo-cycloaddition products in good reaction efficiency and stereoselectivity (48 examples), and has been successfully used in the construction of core skeleton of oncocalyxones, tetracycline and pleurotin. It also provides a reliable method for the late-stage modification of natural products bearing enone groups, such as steroids. The total synthesis of oncocalyxone B was successfully achieved using this PEDA approach.

Date: 2017
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DOI: 10.1038/s41467-017-00440-8

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