Synthesis of a Halicyclamine-Type Macrocyclic Scaffold via Biomimetic Transannular Cyclization
Toshiaki Wayama, Hiroki Oguri
Abstract
Previous attempts for biomimetic transannular reactions between two dihydropyrdine (DHP) rings incorporated in macrocycle frameworks relevant to manzamine alkaloids have been unsuccessful. Herein, we report an efficient regiocontrolled transannular cyclization of C 2 -symmetric macrocyclic precursor with rational modifications of the 3 and 6 positions of the DHP rings to synthesize a halicyclamine-type scaffold. The cis -double bonds installed in the macrocyclic alkyl loops played a crucial role in achieving the biomimetic transannular cyclization.
Topics & Concepts
ChemistryBiomimetic synthesisScaffoldAlkylCombinatorial chemistryStereochemistryDouble bondOrganic chemistryBiomedical engineeringMedicineMarine Sponges and Natural ProductsSynthetic Organic Chemistry MethodsChemical synthesis and alkaloids