Asymmetric Total Synthesis of Iheyamine B
Jiye Jeon, Cheol‐Hong Cheon
Abstract
Herein, we report the first asymmetric total synthesis of iheyamine B from 2,2′-bisindoloazepinone using the stereoselective construction of the trans-vicinal 2-oxopropyl moiety in the azepine scaffold. The asymmetric decarboxylative allylic alkylation provided the α-allylated 2,2′-bisindoloazepinone intermediate. The subsequent conversion of the lactam moiety into another allyl group in a trans-selective manner followed by Wacker oxidation of each allyl unit to the corresponding 2-oxopropyl group completed the total synthesis of iheyamine B.
Topics & Concepts
ChemistryMoietyTotal synthesisAzepineStereochemistryTsuji–Trost reactionStereoselectivityVicinalAlkylationAllylic rearrangementEnantioselective synthesisOrganic chemistryCatalysisAlkaloids: synthesis and pharmacologyChemical synthesis and alkaloidsAsymmetric Synthesis and Catalysis