Ozonolysis of Amino Alkenes Derived From Labda-8(17),14-dien-13-ol

A series of amino alkenes was synthesized from manool [labda-8(17),14-dien-13-ol] as substrates for an investigation of the ability of an amino group to act as an internal nucleophile during ozonolysis. A 10-membered ring keto lactam (20) was produced from amino. alkene (4) but the C8-C9 bond remained intact during the ozonolysis of amino alkene (18). Substrates with an unfavourable relationship of the amino group to the olefin, (7), (10) and (16), gave no products resulting from intramolecular participation.