1611498-63-5Relevant articles and documents
Design and synthesis of a compound library exploiting 5-methoxyleoligin as potential cholesterol efflux promoter
Linder, Thomas,Geyrhofer, Sophie,Papaplioura, Eleni,Wang, Limei,Atanasov, Atanas G.,Stuppner, Hermann,Dirsch, Verena M.,Schnürch, Michael,Mihovilovic, Marko D.
, (2020)
5-Methoxyleoligin and leoligin are natural occurring lignans derived from Edelweiss (Leontopodium nivale ssp. alpinum), displaying potent pro-angiogenic and pro-arteriogenic activity. Cholesterol efflux from macrophages is associated with reverse cholesterol transport which inhibits the development of cardiovascular disease. Within this study, we developed a modular and stereoselective total synthesis of 5-methoxyleoligin which can be readily used to prepare a novel compound library of related analogs. The target 5-methoxyleoligin was synthesized exploiting a recently disclosed modular route, which allows also rapid synthesis of analogous compounds. All obtained products were tested towards macrophage cholesterol efflux enhancement and the performance was compared to the parent compound leoligin. It was found that variation on the aryl moiety in 2-position of the furan ring allows optimization of the activity profile, whereas the ester-functionality does not tolerate significant alterations.
The first stereoselective total synthesis of a new antitumour and anti-inflammatory neolignan, surinamensinol A
Reddy, Parigi Raghavendar,Das, Biswanath
, p. 7432 - 7434 (2014/02/14)
The stereoselective total synthesis of an antitumour and anti-inflammatory 8-O-4′-neolignan, surinamensinol A has been accomplished starting from two aldehydes, 3,4,5-trimethoxy benzaldehyde and vanillin. The key steps involve an asymmetric reduction using a chiral oxazaborolidine complex, a Sharpless asymmetric dihydroxyllation and a Mitsunobu reaction. This is the first report of the total synthesis of surinamensinol A.
