851051-04-2Relevant articles and documents
Biomimetic synthesis of acid-sensitive (-)-caparrapi oxide and (+)-8-epicaparrapi oxide induced by artificial cyclases
Uyanik, Muhammet,Ishibashi, Hideaki,Ishihara, Kazuaki,Yamamoto, Hisashi
, p. 1601 - 1604 (2005)
(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.