6-亚甲基双环[3.2.1]辛-1-烯-3-酮：作为 Diels-Alder 亲二烯体的扭曲烯烃，用于快速合成四种贝壳杉烷二萜。
6-Methylenebicyclo[3.2.1]oct-1-en-3-one: A Twisted Olefin as Diels-Alder Dienophile for Expedited Syntheses of Four Kaurane Diterpenoids.
机构信息
State Key Laboratory of Bioorganic & Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, China.
出版信息
Angew Chem Int Ed Engl. 2019 Oct 28;58(44):15731-15735. doi: 10.1002/anie.201909349. Epub 2019 Sep 17.
6-Methylenebicyclo[3.2.1]oct-1-en-3-one, a twisted and highly reactive enone, was prepared for the first time by elimination of its bromide precursor. Its reactions as a dienophile with several dienes in Diels-Alder reactions proceeded smoothly to provide tricyclic and tetracyclic adducts, which allowed short syntheses (10-11 steps) of four kurane diterpenoids including 11β-hydroxy-16-kaurene, 11α-hydroxy-16-kaurene, liangshanin G, and gesneroidin B.
6-亚甲基双环[3.2.1]辛-1-烯-3-酮是一种扭曲的高反应性烯酮，首次通过消除其溴化物前体来制备。它作为亲二烯体与几种二烯在 Diels-Alder 反应中的反应进行得很顺利，提供了三环和四环加成物，这使得包括 11β-羟基-16-贝壳杉烯、11α-羟基-16-贝壳杉烯、梁山宁 G 和 Gesneroidin B 在内的四种库烷二萜的短合成（10-11 步）成为可能。
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