Asymmetric Total Synthesis and Assignment of Absolute Configuration of Arbornamine
Ying Li, Cheng Wang, Zhiqiang Ma, Kun Zhang, Xue-Tao Xu
Abstract
The asymmetric total synthesis of arbornamine was accomplished in 13 steps, leading to the assignment of its absolute configuration. The key features of the strategy include construction of the C16 quaternary carbon center by a highly diastereoselective Grignard reagent addition to N-tert-butanesulfinylimine, sequential site-selective amidation and N-alkylation to form the C and E rings, and [Ni(COD)2]-mediated Michael addition to close the D ring.
Topics & Concepts
ChemistryAbsolute configurationTotal synthesisReagentAlkylationRing (chemistry)Quaternary carbonStereochemistryEnantioselective synthesisCombinatorial chemistryOrganic chemistryCatalysisChemical synthesis and alkaloidsAsymmetric Synthesis and CatalysisAdvanced Synthetic Organic Chemistry