851050-89-0

Upstream product

• 851051-01-9 (2S,4aR,8aR)-(+)-2-(2,5,5,8a-tetramethyloctahydrochromen-2-yl)ethanol 
• 51694-22-5 ortho-nitrophenyl selenocyanate 
• 147127-72-8 ((2S,3S)-3-((E)-4,8-dimethylnona-3,7-dien-1-yl)-3-methyloxiran-2-yl)methanol 
• 106-28-5 Farnesol 
• 851051-02-0 (-)-2-((2S,4aR,8aR)-2,5,5-8a-tetramethyloctahydrochromen-2-yl)ethyl phenylacetate 

Relevant academic research and scientific papers

Biomimetic synthesis of acid-sensitive (-)-caparrapi oxide and (+)-8-epicaparrapi oxide induced by artificial cyclases

(Chemical Equation Presented) Asymmetric total syntheses of acid-sensitive (-)-caparrapi oxide (1) and (+)-8-epicaparrapi oxide (2) from farnesol (9) were achieved using Sharptess-Katsuki epoxidation and Lewis acid-assisted chiral Bronsted acid (chiral LBA)-induced polyene cyclization as key steps. Furthermore, (-)-1 could be directly synthesized from (S)-nerolidol (3) and (R)-LBA with 88% ds by reagent control which overcame substrate control, while (-)-2 was obtained from (R)-3 and (R)-LBA with >99% ds by the double-asymmetric induction.

Biomimetic synthesis of acid-sensitive (-)- and (+)-caparrapi oxides, (-)- and (+)-8-epicaparrapi oxides, and (+)-dysifragin induced by artificial cyclases

Asymmetric total syntheses of acid-sensitive (-)- and (+)-caparrapi oxides (1) and (+)-8-epicaparrapi oxide (2) from farnesol (10) are achieved using Sharpless-Katsuki epoxidation and Lewis acid-assisted chiral Bronsted acid (chiral LBA)-induced polyene cyclization as key steps. The relative configuration of (+)-dysifragin (4) is determined by a single-crystal X-ray diffraction and its total synthesis is accomplished by the diastereoselective epoxidation of (+)-1. Furthermore, (-)-1 can be directly synthesized from (S)-nerolidol (3) and (R)-LBA with 88% ds by reagent control, which overcame substrate control, while (-)-2 is obtained from (R)-3 and (R)-LBA with >99% ds by the double asymmetric induction.