The first enantioselective synthesis of the chemotactic factor sirenin by an intramolecular [2 + 1] cyclization using a new chiral catalyst

Article abstract of DOI:10.1016/0040-4039(95)01924-7

A simple, highly enantioselective synthesis of sirenin (1) (bioactive form) has been developed which depends on the intramolecular [2 + 1] cycloaddition reaction of diazo ester 5 to form bicyclic ester 6 (95:5 enantioselectivity) using a new and remarkably stable monomeric chiral Cu(I) complex (2) whose structure was proven by X-ray diffraction analysis.