Total synthesis towards briarane skeleton and photoswitchable boron catalysis



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The briarane diterpenoids are a large family of natural products isolated from marine creatures. The briarane skeleton bears a trans-fused[8.4.0]bicyclic system with multiple chirality and functionality. The widely researched amazing biological activities of the briarane family compounds, as well as their challenging bicyclic structures, has promoted a lot of studies in synthesizing the briarane skeleton. Our synthesis efforts toward briarane skeleton are initiated with a dearomatization of a phenol with an electron-withdrawing group, which was rare and lack of examples. A short and brief development of the oxidative dearomatization of the electron-deficient phenols, using μ-oxo-bridged diiodide as an efficient oxidant, was carried and discussed in Chapter 2. The 2,5-cyclohexadienones are a class of molecules bearing multiple functionalities on a 6-membered ring system. Though the studies of its synthesis and utilities bloomed in the past decades, the chemistry of 2,5-cyclohexadiene with an electron-withdrawing group was still unfamiliar to the public. However, with the methodology discussed in Chapter 2, the further synthetic studies towards briarane skeleton will be discussed in Chapter 3, involving in multi-step synthesis sequence and efficient C-C bonds and ring constructions. Independent from the synthetic topic, the photoswitching ability of the azobenzenes was found interesting, particularly with borons attached to it. Photo-induced E-Z isomerization of azobenzenes provides a great opportunity to change the coordination number on the boron center. Warmup research of photo-switched boron species and its potential catalytic application is introduced in Chapter 4.

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Cyclohexadienones, Briarane, Synthesis, Boron, Photoswitching