Asymmetric total syntheses of (+)- and (−)-versicolamide B and biosynthetic implications

Total syntheses of (-)-transtaganolide A, (+)-transtaganolide B, (+)-transtaganolide C, and (-)-transtaganolide D and biosynthetic implications.

Plants belonging to the genus Thapsia have been acknowledged since antiquity for their remarkable medicinal properties. Until very recently, this has been attributed to their primary chemical component thapsigargin (Figure 1a), a widely utilized and structurally complex sesquiterpenoid metabolite known for its potent SERCA inhibition. Within the past decade, an additional group of structurally ...

Total Syntheses of Linear Polythiazole/Oxazole Plantazolicin A and Its Biosynthetic Precursor Plantazolicin B**

Plantazolicin A, a linear decacyclic natural product, exhibits desirable selective activity against the causative agent of anthrax toxicity. The total synthesis of plantazolicin A and its biosynthetic precursor plantazolicin B was successfully achieved by an efficient, unified, and highly convergent route featuring dicyclizations to form 2,4-concatenated oxazoles and the mild synthesis of thiaz...

Total syntheses of subereamollines A and B.

The first total syntheses of (+)- and (-)-subereamollines A and B are reported. The enantiomeric forms of the natural products were obtained by preparative chiral HPLC separation of the corresponding racemates.

Total syntheses of dalesconol A and B.

Catalytic asymmetric total syntheses of quinine and quinidine.

The catalytic, asymmetric syntheses of quinine and quinidine were achieved in 16 steps. The recently developed salen(Al)-catalyzed enantioselective Michael addition of methyl cyanoacetate served to set the crucial C4 stereocenter in 92% ee, and a late-stage asymmetric dihydroxylation was used to differentiate the common intermediate and access the two desired diastereomeric products with high s...