A radical cascade reaction triggered by thiyl radical; an approach toward synthesis of tricyclic structure of platensimycin

GRAPHICAL ABSTRACT

ABSTRACT

The formation of oxa-tricyclic core of platensimycin was attempted. A key precursor of radical cyclization, cyclic anhydride, was readily prepared from diethylmalonate in 6 steps in good yields. Obtained precursor, diallylmethylene-δ-lactone, underwent radical cascade reaction triggered by thiyl radical, giving bicyclic ether in a stereoselective manner.

KEYWORDS:

• Radical cyclization
• radical addition
• platensimycin