(3R,4S)-3,4,8-Trihydroxy-1,2,3,4-tetrahydronaphthalen-1-one monohydrate from Embellisia eureka

Abstract

In the title hydrate, C10H10O4·H2O, the six-membered aliphatic ring that is fused to the benzene ring has a sofa shape, with the hy­droxy group in the 3-position (that represents the sofa back) of the aliphatic ring occupying a quasi-axial position. The hy­droxy group of the aromatic ring is hydrogen-bond donor to the carbonyl O atom; other O—H⋯O hydrogen bonds link the organic mol­ecules and the water mol­ecules into a three-dimensional network.

Asymmetric Synthesis of Natural cis-Dihydroarenediols Using Tetrahydroxynaphthalene Reductase and Its Biosynthetic Implications

“…It shows inhibitory activity toward SHP2, a protein tyrosine phosphatase associated with several forms of cancer, and PTP1B, a negative regulator of the leptin and insulin signaling pathway, as well as phytotoxicity . Despite its common occurrence and rather simple structure, uncertainty remains regarding the stereochemistry of 4 due to conflicting reports in the literature . Various synthetic and biocatalytic methods developed over the years for its preparation could not address this issue completely.…”