手性催化对映选择性全合成 Hypocrolide A。
Catalytic Enantioselective Total Synthesis of Hypocrolide A.
机构信息
Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School , Shenzhen 518055, China.
Department of Chemistry, South University of Science and Technology of China , Shenzhen 518055, China.
出版信息
Org Lett. 2016 Oct 7;18(19):4932-4935. doi: 10.1021/acs.orglett.6b02414. Epub 2016 Sep 13.
The first and catalytic enantioselective total synthesis of hypocrolide A (>99% ee) in 12 steps, as well as other botryanes, is described. The absolute configurations of these compounds have been unambiguously confirmed or reassigned accordingly. The key reactions in this study include an unusual rhodium-catalyzed intramolecular [4 + 2] cycloaddition and a biomimetic oxidative [3 + 2] cycloaddition based on our revised biogenetic pathway.
首次通过 12 步反应实现了 (-)-Hypocrolide A（>99%ee）及其它 botryanes 的对映选择性全合成，这些化合物的绝对构型已被明确确定或重新分配。本研究中的关键反应包括一个不寻常的铑催化的分子内[4+2]环加成反应和一个基于我们修正的生物合成途径的仿生氧化[3+2]环加成反应。
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