28977-57-3Relevant academic research and scientific papers
Mimicking the pineapple scent: Synthesis and properties of (semi)conjugated triene carbonyl derivatives
?i?ka, Peter,Danková, Daniela,Nitrayová, Dária,Fodran, Peter,?pánik, Ivan,Szolcsányi, Peter
, p. 1582 - 1590 (2017)
The unexpected formation of previously nondescribed (semi)conjugated ethyl trienoate revealed its powerful aroma of fresh pineapple. Thus, we have designed, prepared and evaluated a set of its carbonyl analogues as mixtures of (E/Z)-isomers. Although their synthesis from natural ocimene led to target compounds in low yields, optimized preparation from geranyl acetate furnished an aldehyde as high-yielding common intermediate on multigram scale. A series of its Wittig olefinations provided corresponding (E,E)-configured carbonyl dienes. Final acid-catalyzed elimination of allylic acetates provided the desired “pineapple” target in moderate yield. Sensory analysis revealed that only the parent compound possesses the typical pineapple aroma. Although analogous tBu- and/or Bn-esters feature an additional green note, the most similar Me-ester differs by its fresh woody aroma analogously to methyl ketone.
A Synthesis of (+)-Salvadione-A
Majetich, George,Wang, Yanyun,Li, Yang,Vohs, Jason K.,Robinson, Gregory H.
, p. 3847 - 3850 (2003)
(Matrix presented) The p-benzoquinone shown is converted to the novel hexacyclic triterpene salvadione-A in four steps.
Epoxidation of olefins by β-bromoalkoxydimethylsulfonium ylides
Majetich, George,Shimkus, Joel,Li, Yang
supporting information; experimental part, p. 6830 - 6834 (2011/03/18)
Olefins can be converted to their respective epoxides in a one-pot procedure by dissolving the olefin in anhydrous DMSO, adding NBS to the reaction mixture to generate a β-bromoalkoxydimethylsulfonium ylide, and then adding DBU to the reaction mixture. A large variety of alkenes were successfully epoxi-dized with yields largely dependent on the structure of the alkene. Most importantly, the facial selectivity of this one-pot process is the opposite of that observed when using traditional epoxidizing reagents. Electron-poor alkenes are not epoxidized under these conditions.
