Design and Synthesis of Benzosultine-sulfone as a o-Xylylene Precursor via Cross-enyne Metathesis and Rongalite: Further Expansion to Polycyclics via Regioselective Diels-Alder Reaction

Benzosultine-sulfone 5 has been prepared as a o-xylylene or o-quinodimethane precursor by utilization of rongalite. Thermal activation of this hybrid molecule 5 has resulted a new sulfone-based building block 6. Building block 5 is a suitable precursor for the synthesis of unsymmetrically functionalized polycyclics through Diels-Alder (DA) chemistry. The dibromosulfone 24 and benzosultine-sulfone 5 has also been used for the synthesis of various sulfone based unnatural a-amino acid (AAA) derivatives.