The title compound was prepared using acetylstachyflin (I), a fermentation product from Stachybotrys sp. RF-7260, as the starting material. After protection of the phenolic hydroxyl group of (I) as the benzyl ether (II), alcoholysis of its acetate ester with methanolic NaOMe yielded alcohol (III). Oxidation of the secondary alcohol (III) by means of Jones reagent gave rise to ketone (IV). The O-benzyl group of (IV) was finally removed by hydrogenolysis over Pd/C to produce the desired phenol.
Compound SQ-02-S-V2 (I) is isolated from the fermentation broths of Stachybotrys sp. RF-7260 under modified conditions in the presence of DL-valine. Subsequent, methanolysis of the acetate ester group of (I) in the presence of NaOMe gives rise to the title compound.