Photocycloaddition of 2,5-dihydrothiophen SS-dioxides to α,β-unsaturated cyclic anhydrides. Synthesis of 10-hydroxygeraniol
Abstract
10-Hydroxygeraniol (6c) was synthesized from 2,5-dihydro-3-methythiophen SS-dioxide (1b) and citraconic anhydrid (2b) in 48% overall yield via irradiation followed by thermal extrusion of SO2 from the intermediate photoadduct (3b) and a Cope rearrangement of the resulting divinyl diester (5b).