Synthesis of the 10-azatricyclo[3.3.2.04,8]decane core of C 20-diterpenoid alkaloid racemulsonine via iodine(III) promoted transannular aziridination reaction

Article abstract of DOI:10.1021/ol400755x

The functionalized A/E/F ring system of C₂₀-diterpenoid alkaloid racemulsonine has been efficiently synthesized. The Key steps involved a diastereoselective Au(I)-catalyzed annulation to form cis-fused cyclopentene and a PIDA promoted transannular aziridination of primary amine followed by regio- and stereoselective ring cleavage of bridged aziridine.