Towards the total synthesis of keramaphidin B

Towards the total synthesis of keramaphidin B

The enantio- and diastereoselective Michael addition of a δ-valerolactone-derived pronucleophile to a substituted furanyl nitroolefin catalysed by a bifunctional cinchonine-derived thiourea has been used as the key stereocontrolling step in a new synthetic strategy to the heavily functionalised piperidine core of keramaphidin B.

Studies towards the Total Synthesis of Asteriscanolide

Total synthesis of largamide B.

Total synthesis of the cyanobacterial metabolite largamide B and the disproval of its originally assigned stereochemistry as well as confirmation of the revised stereochemistry are reported.

Total Synthesis of Paecilomycin B.

Starting from the glucose-derived δ-lactone and the functionalized aryl bromide, the first total synthesis of naturally occurring paecilomycin B was achieved via functionalized aryl-β-C-glycoside synthesis using 2,4,6-triisopropylphenyllithium under Barbier-type reaction conditions and ring-closing metathesis as the key steps.

Total synthesis of (+/-)-neovibsanin B.

(+/-)-Neovibsanin B was synthesized based on a DMI-accelerated intramolecular Diels-Alder reaction followed by oxy-Michael addition-lactonization. The synthetic (+/-)-neovibsanin B induced similar morphological changes in NGF-mediated PC12 cells compared with natural (+)-neovibsanin B.