97590-65-3Relevant academic research and scientific papers
Total synthesis of TMS-ent-bisabolangelone
Riss, Bernard,Garreau, Marion,Fricero, Prisca,Podsiadly, Patricia,Berton, Nicolas,Buchter, Sophie
, p. 3202 - 3212 (2017)
The absolute configuration of bisabolangelone has been established by an eleven step total synthesis of the corresponding TMS protected antipode starting from (R)-(+)-pulegone. Comparison of the TMS-derivatives by GC on a chiral column, allowed us to assign the absolute configuration of the synthetic compound and thus of the corresponding natural product. The latter has been confirmed by the Mosher's ester analysis of the known secondary carbinol derivative.
Optical Rotatory Dispersion Studies. 138. Synthesis and Conformational Analysis of β-Heteroatom-Substituted Cyclohexanones
Gorthey, Lee Ann,Vairamani, Mariappandar,Djerassi, Carl
, p. 4173 - 4182 (2007/10/02)
Circular dichroism and proton magnetic resonance spectroscopy were used in the conformational analysis of a series of β-heteroatom-substituted cyclohexanones.It was found that the axial population of the substituted ketone relative to that of the monosubstituted cyclohexanone is enhanced for the more highly electronegative substituents oxygen and fluorine and decreased for the less electronegative substituents chlorine, bromine, and sulfur.Possible mechanisms underlying this behavior, including electrostatic and dipole-dipole interactions as well as through-space and through-bond orbital interactions, are briefly discussed.
