After a five-year efforts the XJTU research team led by professor Li Pengfei from the Frontier Institute of Science and Technology found a short and effective synthetic route to tigliane-diterpenoid prostratin from very simple chemicals, cyclopentadiene, through a series of key reactions including epoxide opening, singlet oxygen dearomatization, palladium-catalyzed coupling reactions, ethenyl addition reaction with frustrated Lewis pair, acid- and solvent-controlled stereoselective cyclopropane synthesis, alkene ring closing metathesis, selective oxidation, and so on. Such synthetic strategies as rapid assembly of the tricyclic core and stereoselective construction of multiple consecutive chiral centers provide a foundation to synthesize related diterpenoid products and to conduct researches on medicinal chemistry in the future.
The research result was published in Chem (Impact Factor: 14.104), a flagship research journal of Cell Press in thechemistry field, under the title Total Synthesis of (±)-Prostratin. Doctor Tong Guanghu from the Frontier Institute of Science and Technology is the first author. XJTU Frontier Institute of Science and Technology is the institutional affiliation of the first author and the corresponding author. This research marks a significant breakthrough for professor Li’s research team in total synthesis of natural products after Org.Lett.2014, 16, 2288.
Link to the article: https://www.sciencedirect.com/science/article/pii/S2451929418304765