Total Synthesis of Phyllanemblinin B
Total Synthesis of Phyllanemblinin B: S. Matsumoto, S. Wakamori, K. Nishii, T. Tanaka, H. Yamada
Synlett 2020, 31, DOI: 10.1055/s-0040-1707812
Phyllanemblinin B is a macrocylic compound formed by a d-glucopyranosyl hexahydroxydiphenoyl diester, carrying a β-galloyl side chain. This intriguing natural compound was first isolated in 2001 from the fruit juice of the Malacca tree, which has been reported to have anti-inflammatory and antipyretic properties. Recently, the group of Dr. Shinnosuke Wakamori from the Kwansei Gakuin University (Hyogo, Japan) reported the first total synthesis of phyllanemblinin B, which opens up the perspective of preparing synthetic analogues and performing further studies on the biological properties of these compounds.
Dr. Wakamori said: “To construct the biaryl bond of the hexahydroxydiphenoyl moiety, we focused on the flexibility of the glucopyranose ring. Design and development of the alternative coupling method on the open-chain glucose residue enabled the total synthesis of phyllanemblinin B.”