83988-95-8

Upstream product

• 23838-17-7 umbelliprenine 
• 83998-80-5 C₂₄H₃₁BrO₄ 
• 24163-93-7 farnesyl bromide 
• 93-35-6 7-hydroxy-2H-chromen-2-one 

Relevant academic research and scientific papers

Selective monocyclization of epoxy terpenoids promoted by zeolite NaY. A short biomimetic synthesis of elegansidiol and farnesiferols B-D

Epoxy terpenes cyclize readily, by confinement within zeolite NaY, to form exomethylenic cyclohexanols as the major products. The selective monocyclization of 10,11-epoxyfarnesyl acetate within NaY provides a short and efficient biomimetic route to (±)-elengasidiol and (±)-farnesiferols B-D.

Farnesyloxycoumarins, a new class of squalene-hopene cyclase inhibitors

A few naturally occurring prenyl- and prenyloxycoumarins and several new related synthetic derivatives were evaluated as inhibitors of squalene-hopene cyclase (SHC), a useful model enzyme, to predict their interactions with oxidosqualene cyclase (OSC). Umbelliprenin-10′,11′-monoepoxide (IC50 2.5 μM) and the corresponding 6′,7′-10′, 11′ diepoxide (IC50 1.5 μM) were the most active enzyme inhibitors.

Chemo-enzymatic enantio-convergent asymmetric synthesis of (R)-(+)-Marmin

Asymmetric biohydrolysis of trisubstituted terpenoid oxiranes (rac-1a-rac-3a) was accomplished by employing the epoxide hydrolase activity Rhodococcus and Streptomyces spp. Depending on the biocatalyst, the biohydrolysis proceeded in an enantio-convergent fashion and gave the corresponding vic-diols in up to 97% ee at conversions beyond the 50%-threshold. In order to avoid a depletion of the ee of product by further oxidative metabolism, bioconversions had to be conducted in an inert atmosphere with exclusion of molecular oxygen. The synthetic applicability of this method was demonstrated by the asymmetric total synthesis of the monoterpenoid coumarin (R)-(+)-Marmin in 95% ee.