通过立体选择性 Julia-Kocienski 烯烃化反应全合成对映纯查布罗萘醌 B。
Total Synthesis of Enantiopure Chabrolonaphthoquinone B Via a Stereoselective Julia-Kocienski Olefination.
机构信息
Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Thessaloniki 54124, Greece.
出版信息
J Org Chem. 2021 Aug 6;86(15):10440-10454. doi: 10.1021/acs.joc.1c01106. Epub 2021 Jul 11.
PMID:34247481
Abstract
The total synthesis of cytotoxic meroditerpenoid naphthoquinone derivative chabrolonaphthoquinone B () in an enantiospecific manner is divulged using a chiral pool approach. The key step of our synthetic route is a modified Julia olefination between a sulfone-bearing aliphatic fragment and a Diels-Alder-derived aromatic aldehyde, leading to the stereoselective construction of the -trisubstituted double bond.
摘要
本文采用手性池方法以对映选择性方式全合成细胞毒性梅二萜萘醌衍生物查布罗萘醌 B()。我们合成路线的关键步骤是带有砜基的脂肪族片段和 Diels-Alder 衍生的芳醛之间的改良 Julia 烯丙基化反应，从而立体选择性构建 -三取代双键。
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