35628-05-8Relevant articles and documents
A simple synthesis of (-)-(R)-ipsdienol and (-)-(S)-ipsenol
Draillard, Karine,Lebreton, Jacques,Villieras, Jean
, p. 4281 - 4284 (1999)
A short and efficient synthesis of the unnatural enantiomer of (+)-(S)- ipsdienol 1 and (-)-(S)-ipsenol 2 is presented via an asymmetric allylboration. The synthesis was achieved by using a one-pot reduction- methylenation of an exo-methylene lactone intermediate. (C) 1999 Elsevier Science Ltd.
A synthesis of S-(-)-ipsenol from lactic acid
Trost,Rodriguez
, p. 4675 - 4678 (1992)
A six step synthesis of S-(-)-ipsenol, a constituent of the sex pheromone of the bark beetle, from lactic acid employs an asymmetric aldol condensation and a novel molybdenum catalyzed elimination of an allyl ester as key steps.
Enantioselective Isoprenylboration Reaction of Aldehydes Catalyzed by a Chiral Phosphoric Acid
Zhang, Yu-Long,He, Bo-Jun,Xie, Yi-Wen,Wang, Yu-Hao,Wang, Yi-Long,Shen, Yong-Cun,Huang, Yi-Yong
supporting information, p. 3074 - 3079 (2019/05/15)
The BINOL-derived chiral phosphoric acid (R)-TRIP is utilized as an organocatalyst in the asymmetric isoprenylboration reaction of aldehydes, wherein hydrogen-bond interactions play a key role in the control of enantioselectivity. A wide arrays of enantioenriched dienyl homoallyl alcohols, including two natural products (?)-Ipsdienol and (?)-Ipsenol, have been successfully constituted. The synthetic application to chiral isoprenylated isobenzofuranone, vinyloxirane and cyclohexene derivatives has also been disclosed. (Figure presented.).
Catalytic asymmetric allylic transfer reactions for the Enantioselective synthesis of dienyl and enynyl alcohols
Yu, Chan-Mo,Jeon, Miyoo,Lee, Jae-Young,Jeon, Junha
, p. 1143 - 1148 (2007/10/03)
Efficient catalytic asymmetric allylic transfer reactions of achiral aldehydes with 2-ethynyl- and 2-ethenyl-2-propenyl-stannane promoted by BINOL-TiIV complex with synergetic reagent are achieved for the synthesis of homoenynyl- and dienyl alcohols with high levels of enantioselectivity. The range of enantioselectivity is 84-99% ee with good chemical yields. The application of catalytic asymmetric dienylation in a single operation was exemplified by the enantioselective synthesis of naturally occurring (-)-Ipsdienol and (-)-Ipsenol.