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Enantioselective Total Syntheses of Pentacyclic Homoproaporphine Alkaloids

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journal contribution
posted on 16.09.2020 by Liu-Yang Pu, Fan Yang, Ji-Qiang Chen, Ying Xiong, Huai-Yu Bin, Jian-Hua Xie, Qi-Lin Zhou
Herein we report the first enantioselective total syntheses of pentacyclic homoproaporphine alkaloids by means of a route, which includes a tandem retro-oxa-Michael addition and nucleophilic substitution to generate the oxa-benzobicyclco[3.3.1]­nonane core structure, a Pictet–Spengler cyclization to construct the fused B and C rings, and sequential Baeyer–Villiger oxidation and pinacol-type cyclization to install the hydroxyl-lactol moiety of D ring. With this unified route, six pentacyclic homoproaporphine alkaloids have been synthesized enantioselectively.

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