71687-74-6Relevant academic research and scientific papers
Enantioselective synthesis of the tricyclic core of (+)-strigol
Takahashi, Aiko,Ogura, Yusuke,Enomoto, Masaru,Kuwahara, Shigefumi
, p. 6634 - 6639 (2016/09/28)
An enantioselective synthesis of the tricyclic core structure of (+)-strigol, a potent seed germination stimulant for root parasitic weeds, has been achieved from 2-iodo-4,4-dimethyl-2-cyclohexen-1-one in 14 steps. The key steps include a CBS reduction of an iodo enone to obtain a cyclohexenol derivative of high enantiomeric excess, regioselective epoxide ring opening with a Grignard reagent in a low-polarity solvent, highly diastereoselective addition of vinyllithium to a ketone, and Lewis acid-promoted installation an acetate unit onto a bicyclic allylic acetate intermediate.
Enzymatic resolution of racemic secondary cyclic allylic alcohols
Winska, Katarzyna,Grudniewska, Aleksandra,Chojnacka, Anna,Bialonska, Agata,Wawrzenczyk, Czeslaw
experimental part, p. 670 - 678 (2010/08/07)
The resolutions of five racemic cyclic alcohols: 6,6-dimethylcyclohex-2-en-1-ol (±)-5, 4,4-dimethylcyclohex-2-en-1-ol (±)-7, 5,5-dimethylcyclohex-2-en-1-ol (±)-11 and isomeric trans-(±)-13 and cis-piperitols (±)-14 are presented. They were resolved by enzymatic esterification with vinyl esters or by enzymatic hydrolysis of their racemic esters in phosphate buffer. The following lipases were used as biocatalysts: Novozyme 435 (Candida antarctica), Amano PS (Burkholderia cepacia) and lipase from Candida cylindracea. All isomers of alcohols were obtained with at least 96% ee.
