Synthesis of Bridged Alkaloid-like Scaffolds through Sequential Rearrangement of Sulfur Ylides and 2-Hydroxy-β-nitrostyrenes

A two-component, three-molecule cascade reaction between sulfur ylides and 2-hydroxy-β-nitrostyrenes is developed for the efficient and stereoselective synthesis of complex polycyclic alkaloid-like scaffolds. This metal-free protocol proceeds smoothly under mild conditions using readily available materials, affording structurally diverse products in good yields with excellent diastereoselectivity. A plausible mechanism is proposed.