Abstract:
The synthesis of a series of 5,5-, 5,6-, and 6,6-monobenzannulated spiroketals using a novel cross-metathesis-radical-cyclisation approach is reported. Cross metathesis between two olefin coupling partners resulted in the formation of a heterodimer which upon hydrogenation furnished a saturated alcohol product. Oxidative radical cyclisation then afforded the desired monobenzannulated spiroketals in good overall yield.