Ming-Ming Li

Polycyclic Polyprenylated Acylphloroglucinol Congeners Possessing Diverse Structures from Hypericum henryi.

Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a class of hybrid natural products sharing the mevalonate/methylerythritol phosphate and polyketide biosynthetic pathways and showing considerable structural and bioactive diversity. In a systematic phytochemical investigation of Hypericum henryi, 40 PPAP-type derivatives, including the new compounds hyphenrones G-Q, were obtained. These compounds represent 12 different structural types, including four unusual skeletons exemplified by 5, 8, 10, and 17. The 12 different core structures found are explicable in terms of their biosynthetic origin. The structure of a known PPAP, perforatumone, was revised to hyphenrone A (5) by NMR spectroscopic and biomimetic synthesis methods. Several compounds exhibited inhibitory activities against acetylcholinesterase and human tumor cell lines. This study deals with the structural diversity, function, and biogenesis of natural PPAPs.

Concise synthesis of (±)-Lingzhiol via epoxy-arene cyclization

Concise synthesis of (±)-Lingzhiol has been achieved. The key reaction involves one-step construction of a 5/5/6/6 tetra-ring backbone of Lingzhiol via epoxy-arene cyclization.

One-Step Semisynthesis Method of Spirocurcasone and Pyracurcasone from Curcusones A and B

High contents of curcusones A and B and trace amounts of spirocurcasone exist in the roots of Jatropha curcas. Here, a one-step semisynthesis method of spirocurcasone and pyracurcasone was built, not only resulted an increased yield of spirocurcasone but also produced pyracurcasone, which exhibited greater cytotoxicity compared to curcusones A and B. The plausible mechanism of the formation of pyracurcasone was proposed, and the proposed biogenetic origin for spirocurcasone by Taglialatela-Scafati was confirmed.

Total synthesis of 1-oxomiltirone via Suzuki coupling

Abietane diterpenes and miltirone series have shown important activities and for medical purposes in order to achieve the total synthesis of 1-oxomiltrone 1 and miltirone 4, a versatile intermediate 6 was found. The compound 6 could be used as a precursor A-B-C rings with different oxidative degrees in selected abietane diterpenes when synthesized through high yield Suzuki reaction and subsequent cyclization, and total synthesis of 1-oxomiltirone (1) has been achieved.

Catalytic Asymmetric Formal Total Synthesis of (−)-Triptophenolide and (+)-Triptolide

Catalytic asymmetric formal synthesis of (−)-Triptophenolide and (+)-Triptolide have been achieved. Key reaction involves Palladium catalyzed asymmetric conjugate addition of aryl boronic acid to 3-methyl cyclohexe-1-none to form quaternary carbon. Claisen rearrangement and subsequent aldol reaction furnished trans-decaline key intermediate, which assured a formal total synthesis of (−)-Triptophenolide and (+)-Triptolide.Graphical Abstract