Synthesis of Deoxyaspidodispermine Based on a Functional Protecting Group Strategy
Kouassi Signo, Sylvain Canesi
Abstract
A synthesis of deoxyaspidodispermine was produced from homotyramine. This approach is based on the application of a functional protecting group strategy that not only masks the reactivity of sensitive groups during crucial steps but also possesses a moiety desired in the final target, which is transferred to the substrate at the time of deprotection. This synthesis highlights an aza-Michael-Smiles ring-closure cascade, which enables the formation of a tetracyclic system from a nosylamide protecting group.
Topics & Concepts
ChemistryMoietyProtecting groupFunctional groupCombinatorial chemistryReactivity (psychology)Ring (chemistry)Group (periodic table)Substrate (aquarium)StereochemistryOrganic chemistryMedicineOceanographyAlkylPathologyPolymerGeologyAlternative medicineAlkaloids: synthesis and pharmacologyChemical synthesis and alkaloidsAxial and Atropisomeric Chirality Synthesis