72627-53-3Relevant academic research and scientific papers
A general approach to the asymmetric synthesis of lignans: (-)-methyl piperitol, (-)-sesamin, (-)-aschantin, (+)-yatein, (+)-dihydroclusin, (+)-burseran, and (-)-isostegane
Enders, Dieter,Lausberg, Vivien,Del Signore, Giuseppe,Berner, Otto Mathias
, p. 515 - 522 (2007/10/03)
A highly efficient, diastereo- and enantioselective route was developed to access a great variety of lignans. The asymmetric synthesis of the 2,3-disubstituted γ-butyrolactones 9a-c could be improved in the case of aldol reactions by employing 2.2 equivalents of LiCl as an additive to provide, after purification, highly diastereo- and enantioenriched starting materials for the synthesis of the furofuran lignans (-)-methyl piperitol, (-)-sesamin, and (-)-aschantin. Furthermore, the γ-butyrolactone 15 was converted into dibenzylbutyrolactone lignan (+)-yatein, the dibenzylbutandiol type (+)-dihydroclusin, the tetrahydrofuran type (+)-burseran, and the dibenzocyclooctadiene type (-)-isostegane.
A KEY INTERMEDIATE FOR THE SYNTHESIS OF ANTITUMOR LIGNAN PROTOTYPES
Belletire, J. L.,Fremont, S. L.,Fry, D. F.
, p. 699 - 710 (2007/10/02)
Procedures are described for the convenient generation of an iodinated carboxylic acid possessing considerable utility as a precursor to several biologically active lignans.
