Total synthesis of cleomiscosin C via a regioselective cycloaddition reaction of o-quinone

A. Kuboki, C. Maeda, T. Arishige, K. Kuyama, M. Hamabata, S. Ohira

We have achieved total synthesis of cleomiscosin C (aquillochin) (I) through regioselective cycloaddition of o-quinone II and protected sinapyl alc. III as a key step. During preparation of the o-quinone from phenol by IBX oxidation, silyl substituents adjacent to the phenolic hydroxyl group afforded effective inhibition of an undesired oxidative elimination.

Tetrahedron Letters

Elsevier Ltd.

49

29-30

4516

4518