Please use this identifier to cite or link to this item: https://scholarbank.nus.edu.sg/handle/10635/151083
Title: MEDIUM-SIZED RING SYNTHESIS VIA PALLADIUM-CATALYZED CYCLOADDITION
Authors: WANG YANONG
Keywords: medium-sized rings, [6+4] cycloaddition, [8+4] cycloaddition, palladium, heterocycles, homogeneous catalysis
Issue Date: 23-Aug-2018
Citation: WANG YANONG (2018-08-23). MEDIUM-SIZED RING SYNTHESIS VIA PALLADIUM-CATALYZED CYCLOADDITION. ScholarBank@NUS Repository.
Abstract: Medium-sized rings are found in various biologically active natural products. However, the great challenges in synthesis extremely limit their application in drug discovery due to the unfavorable transannular interactions and high entropic barrier. In this dissertation, we have developed the efficient strategies to construct various medium-sized cycles based on Pd-catalyzed formal cycloaddition. Firstly, we have described a stereoselective and divergent methodology to prepare the synthetically challenging bicyclo[5.5.0]dadocatrienes, bicyclo[4.4.1]undecanones and bridgehead olefinic [4.4.1] bicycles by the formal cycloaddition of readily available tropone. More importantly, the extensive mechanistic studies disclosed the intriguing mechanism: two diastereomeric intermediates play an important role in the products distribution. Besides, we documented the first enantioselective [6+4] cycloaddition of vinyl oxetanes with azadienes to build benzofuran- or indole-fused ten-membered heterocycles. The commercially available chiral Pd-SIPHOX catalyst can deliver a wide range of ten-membered heterocycles in excellent enantioselectivity and yield.
URI: http://scholarbank.nus.edu.sg/handle/10635/151083
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