Synthesis of (+)-epicolidine C and the 6/6/6/5 tetracyclic core of spylidone

Haoran Dong, Xiaoguang Lei

Tetrahedron Letters, 2024, 146, 155181.


The first total synthesis of (+)-epicolidine C has been accomplished via a late-stage HfCl4-mediated epoxide opening from (+)-PF1052. The 6/6/6/5 tetracyclic core of spylidone has also been constructed from (+)-AB4015-B via late-stage iodine(I)- or manganese(III)-mediated oxidative cyclization reactions, whose absolute stereostructure was unambiguously confirmed by X-ray crystallographic analysis.