Total synthesis of potent antifungal marine bisoxazole natural products bengazoles A and B.

The bengazoles are a family of marine natural products that display potent antifungal activity and a unique structure, containing two oxazole rings flanking a single carbon atom. Total syntheses of bengazole A and B are described, which contain a sensitive stereogenic centre at this position between the two oxazoles. Additionally, the synthesis of 10-epi-bengazole A is reported.

Sulfoximines as ligands in copper-catalyzed asymmetric vinylogous Mukaiyama-type aldol reactions.

[reaction: see text] gamma,delta-Unsaturated alpha-hydroxy diesters with quaternary centers have been obtained with up to 99% ee in high yields using catalysts prepared from copper(II) triflate and C(1)-symmetric aminosulfoximines.

Highly modular synthesis of C1-symmetric aminosulfoximines and their use as ligands in copper-catalyzed asymmetric Mukaiyama-aldol reactions.

The development of C1-symmetric aminosulfoximines, their highly modular synthesis, and their application in enantioselective copper-catalyzed Mukaiyama-type aldol reactions between pyruvates and enolsilanes is described. In this context, the influence of the ligand architecture as well as the optimization of the reaction conditions are discussed. In detail, the dependence of the catalyst efficiency on the solvent, the metal source and the temperature are reported, and an interesting additive effect is highlighted.