56459-16-6Relevant articles and documents
Asymmetric Synthesis of Carbocyclic Propellanes
Schneider, Lisa M.,Schmiedel, Volker M.,Pecchioli, Tommaso,Lentz, Dieter,Merten, Christian,Christmann, Mathias
supporting information, p. 2310 - 2313 (2017/05/12)
A modular synthesis of functionalized carbocyclic propellanes was developed. Formation of the first of two quaternary bridgehead centers has been achieved by desymmetrization of prostereogenic ketones by either Hajos-Parrish-Eder-Sauer-Wiechert-type processes or Werner’s catalytic asymmetric Wittig reaction. The obtained bicyclic enones were subjected to conjugate additions upon which the remaining ring was formed by olefin metathesis. All bridges are amenable to further derivatization, which renders those compounds useful as central units in fragment-based drug discovery or as ligand scaffolds.
An efficient synthesis of (±)-frondosin B using a Stille-Heck reaction sequence
Masters, Kye-Simeon,Flynn, Bernard L.
scheme or table, p. 1290 - 1292 (2010/06/18)
A concise, convergent synthesis of (±)-frondosin B has been developed based on the application of a Stille-Heck reaction sequence of 2-chloro-5-methoxybenzo[b]furan-3-yl triflate and 2-(3-butenyl)-3- (trimethylstannyl)cyclohex-2-enone giving the racemic natural product in a 34% overall yield.
Characterization of the key aroma compounds in apricots (Prunus armeniaca) by application of the molecular sensory science concept
Greger, Veronika,Schieberle, Peter
, p. 5221 - 5228 (2008/02/10)
An aroma extract dilution analysis applied on an aroma distillate prepared from fresh apricots revealed (R)-γ-decalactone, (E)-β-damascenone, δ-decalactone, and (R/S)-linalool with the highest flavor dilution (FD) factors among the 26 odor-active compounds identified. On the basis of quantitative measurements performed by application of stable isotope dilution assays, followed by a calculation of odor activity values (OAVs), β-ionone, (Z)-1,5-octadien-3-one, γ-decalactone, (E,Z)-2,6-nonadienal, linalool, and acetaldehyde appeared with OAVs >100, whereas in particular certain lactones, often associated with an apricot aroma note, such as γ-undecalactone, γ-nonalactone, and δ-decalactone, showed very low OAVs (5). An aroma recombinate prepared by mixing the 18 most important odorants in concentrations as they occurred in the fresh fruits showed an overall aroma very similar to that of apricots. Omission experiments indicated that previously unknown constituents of apricots, such as (E,Z)-2,6-nonadienal or (Z)-1,5-octadien-3-one, are key contributors to the apricot aroma.
Generation of Azomethine Ylides via the Desilylation Reaction of Immonium Salts
Padwa, Albert,Haffmanns, Gunter,Tomas, Miguel
, p. 3314 - 3322 (2007/10/02)
Generation of intermediates having azomethine ylide reactivity was achieved by the reaction of several ethanol or thioimidate derivatives with methyl iodide followed by treatment of the resulting imine with (trimethylsilyl)methyl triflate.Desilylation of
