Enantioselective construction of <i>cis</i>-hydroindole scaffolds <i>via</i> an asymmetric inverse-electron-demand Diels–Alder reaction: application to the formal total synthesis of (+)-minovincine
Fangqing Zhang, Bing-Tao Ren, Yuqiao Zhou, Yangbin Liu, Xiaoming Feng
Abstract
-hydroindole derivatives bearing multiple contiguous stereocenters and functional groups were obtained in good to excellent yields and enantioselectivities (up to 99% yield, and 95% ee) under mild reaction conditions. Moreover, the enantioselective formal total synthesis of (+)-minovincine was concisely furnished with high efficiency and stereoselectivity to demonstrate the synthetic potential of this method.
Topics & Concepts
Enantioselective synthesisInverseDiels–Alder reactionFormal synthesisChemistryTotal synthesisCatalysisMathematicsStereochemistryOrganic chemistryGeometryChemical synthesis and alkaloidsAsymmetric Synthesis and CatalysisMicrobial Natural Products and Biosynthesis