Synthesis of 8‐Hydroxygeraniol

Abstract

This article describes the procedure for synthesis of 8‐hydroxygeraniol, which is a key biosynthetic precursor to all monoterpene indole alkaloids (MIAs). It presents some of the important points to be considered, the conditions that need to be maintained, characterization data, and the reagents required, as well as the techniques used and the equipment setup that are vital to carrying out the process. The article also describes the hazards associated with working with chemicals and the ways to deal with these hazards. The notorious poison strychnine is just one example of an MIA that arises biosynthetically from strictosidine. Other examples including medicinally important compounds such as the anti‐cancer agent vinblastine, the antimalarial medicine quinine, and ajmalicine, used to treat high blood pressure. Two reports were disclosed in 1970, which involved the use of either levulinaldehyde or dehydrolinalool to prepare 8‐hydroxygeraniol through multistep synthetic sequences.

Construction of oxime ester derivatives of osthole from Cnidium monnieri, and evaluation of their agricultural activities and control efficiency

“…A mixture of osthole (1, 1 mmol, Fig. 2) and selenium dioxide (SeO 2 , 1 mmol) in glacial acetic acid (5 mL) was stirred at 80°C for 3 h. 27 When the reaction was complete, ice water (10 mL) was added to the mixture, which was extracted with dichloromethane (20 mL × 3). Then the combined organic phase was dried over anhydrous sodium sulfate (Na 2 SO 4 ), concentrated in vacuo and purified by preparative thin-layer chromatography (PTLC) eluting with petroleum ether/ethyl acetate (v/v = 2/1) to afford compound 2.…”