Xu Ze-Jun, Tan Dong-Xing, Wu Yikang
State Key Laboratory of Bioorganic and Natural Product Chemistry, Collective Innovative Center for Chemistry and Life Sciences, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Road, Shanghai 200032, China.
Org Lett. 2015 Oct 16;17(20):5092-5. doi: 10.1021/acs.orglett.5b02599. Epub 2015 Oct 5.
In connection with its first synthesis, plakinidone was structurally revised to a five-membered lactone. The key evidence for the previous assignment of this natural product as a perlactone was proven to be a misinterpretation of the MS data because of unawareness of a facile air oxidation. The synthetic samples also allowed for detection of differences in (13)C NMR for diastereomers of remote stereogenic centers, along with the influence of the air oxidation on the optical rotation.
在首次合成过程中，普拉基尼酮的结构被修正为五元内酯。之前将这种天然产物归为过内酯的关键证据被证明是对质谱数据的错误解读，原因是未意识到其易发生空气氧化。合成样品还使得能够检测到远程手性中心非对映异构体在碳-13核磁共振方面的差异，以及空气氧化对旋光性的影响。
