The Synthesis and ¹³C-NMR Spectrum of 1,4-Dioxaspiro(4.5)deca-6,9-dien-2,8-dione

Abstract

Recently there has been a great deal of interest in the preparation and use of selectively blocked quinones. Thus, Evans¹ has used p-quinone monoketals and silyl cyanohydrin derivatives in synthetic studies. The parent p-benzoquinone mono(ethylene)ketal has been prepared². Deslongchamps and co-workers³ used a spirolactone blocked o-quinone in an elegant total synthesis of ryanodol. Likewise, Wiesner⁴ has used a spirolactone blocked o-quinone in the synthesis of the C/D ring systems of chasmanine and napelline. Our interest in selective carbonyl-blocked quinones for synthesis led us to prepare the parent spirolactone blocked p-benzoquinone; 1,4-dioxaspiro(4.5)deca-6,9-dien-2,8-dione (1).