Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky , 789 South Limestone Street, Lexington, Kentucky 40536, United States, and Division of Cardiovascular Medicine, Gill Heart Institute, and Markey Cancer Center, University of Kentucky , 741 South Limestone Street, Lexington, Kentucky 40536, United States.
Org Lett. 2013 Nov 1;15(21):5566-9. doi: 10.1021/ol4027649. Epub 2013 Oct 23.
An efficient diastereoselective oxa-Pictet-Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.
发展了一种高效的非对映选择性氧杂-Pictet-Spengler 反应策略，用于构建苯并异色满非对映异构体。该反应在天然存在的吡喃并萘醌 (+)-frenolicin B 和 epi-(+)-frenolicin B 以及一系列 frenolicin 前体类似物的全合成中得到了应用。该方法具有通用性，提供了极好的立体选择性，因此为吡喃并萘醌类似物的合成提供了一个合成进展。
