223751-40-4Relevant academic research and scientific papers
Nondynamic and dynamic kinetic resolution of lactones with stereogenic centers and axes: Stereoselective total synthesis of herbertenediol and mastigophorenes A and B
Bringmann, Gerhard,Pabst, Thomas,Henschel, Petra,Kraus, Juergen,Peters, Karl,Peters, Eva-Maria,Rycroft, David S.,Connolly, Joseph D.
, p. 9127 - 9133 (2007/10/03)
The stereoselective total synthesis of the sesquiterpene herbertenediol (3) and of its naturally occurring dimers, mastigophorenes A [(P)-1] and B [(M)-1], is described. Following the 'lactone concept', the configuration at the biaryl axis was atropo-dive
Total syntheses of (-)-herbertenediol, (-)-mastigophorene A, and (-)- mastigophorene B. Combined utility of chiral bicyclic lactams and chiral aryl oxazolines
Degnan, Andrew P.,Meyers
, p. 2762 - 2769 (2007/10/03)
A nonracemic bicyclic lactam has been used to construct a chiral cyclopentane containing vicinal quaternary carbon centers in optically pure form, which is common to all of the title compounds. An oxazoline-mediated asymmetric Ullmann coupling was then utilized to establish chirality about the biaryl axis of mastigophorenes A and B. Through the course of this synthesis, it was clearly demonstrated that smaller chiral auxiliaries lead to higher levels of atroposelection, a previously unknown phenomenon of the asymmetric Ullmann coupling.
