222022-94-8Relevant articles and documents
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
First synthesis of mastigophorenes A and B, by biomimetic oxidative coupling of herbertenediol
Bringmann, Gerhard,Pabst, Thomas,Rycroft, David S.,Connolly, Joseph D.
, p. 483 - 486 (2007/10/03)
The first synthesis of mastigophorenes A and B by oxidative phenolic coupling of partially protected derivatives of their joint natural monomeric half, herbertenediol, is described. The synthesis starts from this diol itself or from the corresponding aldehyde, both available by isolation from the liverwort, Herbertus aduncus. After transformation of herbertenediol to a chemically appropriate monophenolic coupling precursor, the oxidative dehydrodimerization was brought about using (tert-BuO)2, followed by deprotection to give mastigophorenes A and B in their 'natural' atropisomeric ratio, as isolated from the liverwort.